Preparative Organic Photochemistry, Softcover reprint of the original 1st ed. 1968

(Abridged and translated) Organic photochemistry may be divided into three parts: theory which is the province of the physical chemist; instrumentation which requires the skill of both physicist and engineer; and preparation which falls within the sphere of the organic chemist. At one time the same person could cover all three fields without too much difficulty, but this has now become virtually impossible because the disciplines involved have expanded in both breadth and depth; it is there­ fore timely to have a separate treatment of preparative organic photo­ chemistry. There appears to be no review of the main photochemical reactions which includes the advances made in recent years available to the organic chemist working in the preparative field. An exception is the excellent "Photochemical Reactions" by C. R. MASSON, V. BOEKELHEIDE and W. A. NoYES JR., published in 1956, which gives a brief review of the reactions which are important in preparative organic photochemistry. The present monograph on the other hand seeks to provide a detailed survey for the chemist; the author does not set out to discuss every photo­ chemical reaction in the field of organic chemistry but he does include in addition to those of current interest in the preparative field some which are likely to be of interest in the future and which result in single end-products of known composition. The photochemical synthesis of highly polymerized products falls outside the scope of the work.

1 Photoisomerization of unsaturated systems proceeding with the formation of four-membered homocyclic rings.- 1. Formation of cyclobutane derivatives by intramolecular addition between non-conjugated olefinic linkages (Ciamician-addition).- 2. Photochemical valence tautomerization of 1,3-dienes.- a) Homoannular 1,3-dienes.- b) Aromatic compounds.- c) Transoid 1,3-dienes.- 3. Intramolecular dianthracene formation.- References.- 2 Photoisomerization of dienes and trienes not leading to the formation of cyclobutane derivatives.- 1. Photoisomerization of open chain 1,3-dienes to 1,2-dienes.- 2. Photoisomerization of 1,3-cyclohexadienes.- a) Cleavage to 1,3,5-hexatrienes.- b) Rearrangement to bicyclo[3.1.0]hex-2-enes.- 3. Photoisomerization of 1,5-cyclooctadienes.- 4. Photoisomerization of 1,3,5-hexatrienes to 1,3-cyclohexadienes.- 5. Photoisomerization of an acene involving loss of aromaticity.- References.- 3 Photoisomerization of aldehydes and ketones not leading to the formation of oxygen heterocycles.- 1. Photoisomerization of ?, ?-unsaturated carbonyl compounds to ?, ?-unsaturated or cyclopropyl isomers.- 2. Photoenolization of aromatic ketones.- 3. Photoisomerization of saturated ketones via photoelimination.- 4. Photoisomerization of ?, ?-unsaturated carbonyl compounds via cyclization.- a) Cyclization of citral.- b) Rearrangement of eucarvone.- c) Rearrangement of verbenone.- 5. Photoisomerization of cross-conjugated cyclohexadienones.- a) Simple 2,5-cyclohexadien-l-ones.- b) Condensed 2,5-cyclohexadien-l-ones.- References.- 4 Various photoisomerizations of ketones, esters and halides.- 1. Isomerization of ketones to tertiary alcohols by intramolecular cyclization.- a) Cyclobutanols from saturated cyclic and acyclic ketones.- b) 2-Hydroxycyclobutanones from 1,2-diketones.- c) Cyclobutanols in the steroid series.- d) Cyclohexenols from non-conjugated ketones.- 2. Photorearrangement of enol and dienol esters.- 3. Isomerizations with migration of bromine atoms.- 4. Light-induced von Auwers rearrangement.- References.- 5 Photoisomerizations involving formation and transformation of five or six membered heterocyclic oxygen compounds.- 1. Photochemical formation of heterocyclic oxygen compounds.- a) Formation of furan derivatives by intramolecular cyclization.- b) Formation of pyran derivatives by intramolecular cyclization.- c) Formation of heterocyclic oxygen compounds by isomerization of cyclic ketones.- 2. Photoisomerization of heterocyclic oxygen compounds to open chain compounds.- a) Photoisomerization of furan derivatives.- b) Photoisomerization of cyclic acetais to esters.- 3. Photochemical rearrangements among heterocyclic oxygen compounds.- a) Isomerization of a 4H-pyran to a 2H-pyran.- b) Isomerization of epidioxides.- References.- 6 Photoisomerizations involving nitrogen compounds.- 1. Photoisomerizations with rupture of nitrogen-oxygen bonds.- a) Amides from aldoximes.- b) Anilides from nitrones.- c) Oxaziridines from nitrones.- d) Unsaturated lactams from heterocyclic N-oxides.- e) 2-Hydroxyazobenzenes from azoxybenzenes.- 2. Photoisomerization with rupture of nitrogen-halogen bonds.- 3. Photoisomerizations with rupture of nitrogen-carbon bonds.- a) Rearrangement of a pyrimidine.- b) Rearrangement of pyrazoles.- References.- 7 Photochemical stereoisomerization.- 1. Photochemical cis-trans isomerizations at double bonds.- a) Compounds containing isolated C=C bonds.- b) Dienes and polyenes.- c) Indigoid systems.- d) Azo compounds.- e) Compounds containing C=N bonds.- 2. Photochemical cis-trans isomerizations of cyclopropane and cyclobutane derivatives.- 3. Photoepimerizations.- a) Epimerization at carbon atoms.- b) Epimerization at sulfur atoms.- References.- 8 Photodimerization with formation of cyclobutane derivatives (Cyclodimerization).- 1. Stilbene and related compounds.- 2. Unsaturated hydrocarbons.- a) Acyclic dienes.- b) Cyclic olefins.- c) Cyclic dienes.- 3. a,ß-Unsaturated ketones.- a) Acyclic ?, ?-unsaturated ketones.- b) Cyclic a,ß-unsaturated ketones.- c) 1,4-Quinones.- 4. ?, ?-Unsaturated acids and related compounds.- a) Derivatives of maleic and fumaric acids.- b) Cinnamic acids.- 5. Coumarin and isocoumarin.- a) Coumarin.- b) Isocoumarin.- c) Furocoumarins.- 6. 2,6-Dimethyl-4-pyrone.- 7. Tetraphenylbutatriene.- 8. Unsaturated sulfur compounds.- a) Benzo[b]thiophene 1,1-dioxide.- b) 2-Nitrobenzo-l,4-dithiin.- 9. Thymine and related pyrimidine derivatives.- 10. ß-Lumicolchicine.- 11. Acetylene compounds.- References.- 9 Photodimerizations involving formation of eight-membered rings.- 1. Carbocyclic aromatic compounds.- a) Naphthalene derivatives.- b) Anthracene and derivatives.- c) Higher condensed aromatic compounds.- 2. Heterocyclic nitrogen compounds.- a) Pyridine derivatives.- b) Condensed nitrogen heterocyclic compounds.- 3. Heterocyclic oxygen compounds.- References.- 10 Various photodimerizations involving aldehydes, halides and thiocarbonyl compounds.- 1. Photodimerization of aliphatic compounds.- a) Butyraldehyde.- b) Dimerization of halides.- c) Dimerization of thiocarbonyl compounds.- 2. Photodimerizations of aromatic aldehydes.- References.- 11 Cycloaddition of alkenes or alkynes to other alkenes or aromatic nuclei leading to the formation of four-membered rings. Photolyses involving retro-cycloaddition.- 1. Addition of maleic anhydride to benzene and related aromatic compounds including furan and thiophene.- 2. Addition of maleic acid derivatives to alkenes.- 3. Addition of 2-methyl-2-butene to benzonitrile.- 4. Photochemical cycloaddition of ?, ?-unsaturated ketones to alkenes.- a) 2-Cyclohexenone and isobutylene.- b) Cyclopentenone and cyclopentene.- c) 2,4-Pentanedione or dimedone and cyclohexene.- 5. Photochemical cycloaddition reactions of acetylene compounds.- a) Addition to benzene and derivatives.- b) Addition to cyclopentenone.- c) Addition to dimethyl cyclobutene-l,2-dicarboxylate.- d) Addition of diphenyl acetylene to naphthalene.- 6. Photolyses involving retro-cycloaddition.- a) Photolysis of dehydronorcamphor.- b) Photochemical synthesis of bullvalene via retro-cycloaddition 116 References.- 12 Photochemical cycloaddition of 1,2-quinones, 1,2-diketones and 1,2,3-triketones to multiple bonds.- Photochemical cycloaddition of 1,2-quinones, 1,2-diketones and 1,2,3-triketones to multiple bonds.- References.- 13 Photochemical cyclization of aromatic compounds via elimination of hydrogen and/or halogen atoms. Formation of carbocycles.- 1. Formation of five-membered homocycles. A fluorene derivative from triphenyl-methyl.- 2. Formation of six-membered homocycles.- a) Phenanthrenes from stilbenes.- b) Fused aromatic compounds from o-dibenzylidene compounds.- c) Phenanthroperylenediones, dibenzoperylenediones and analogous compounds from less condensed aromatic precursors.- d) Dehydrocyclization of some fused heterocyclic hydrocarbons.- References.- 14 Photochemical dehydrocyclization of aromatic compounds via elimination of hydrogen atoms. Formation of heterocycles.- 1. Formation of five-membered heterocycles. Carbazoles from diphenylamines.- 2. Formation of six-membered heterocycles.- a) Benzocinnolines from azobenzenes.- b) Phenanthridines from Schiffs bases.- c) Phenanthridizinium salts from styrylpyridinium salts.- d) Benzo[c]tetrazolo[2,3-a]cinnolinium salts from triphenyltetrazolium salts 143.- References.- 15 Photochemical dehydrodimerization.- 1. Dehydrogenation by oxygen.- 2. Dehydrogenation by carbonyl compounds.- 3. Dehydrogenation by dyes.- 4. Dianthracene from dihydroanthracene.- References.- 16 Photochemical dehydrogenation.- 1. Quinones as dehydrogenating agents.- 2. 1,2-Disulfides as dehydrogenating agents.- 3. Photosensitized dehydrogenation using dyes.- References.- 17 Photochemical additions to carbon-carbon multiple bonds not resulting in ring formation.- 1. Water.- 2. Hydrogen peroxide (Milas reaction).- 3. Hydrogen bromide.- 4. Nitrosyl chloride.- 5. Alcohols, ethers, and tert. butyl hypochlorite.- a) Alcohols.- b) Ethers.- c) Tert. butyl hypochlorite.- 6. Sulfur compounds.- a) Hydrogen sulfide, thiols and thiocarboxylic acids.- b) Sulfenyl chlorides.- c) Sulfonyl chlorides.- 7. Ammonia, amines and formamide.- a) Ammonia and amines.- b) Formamides.- 8. Dimethylmaleic anhydride.- 9. Aldehydes and ketones.- a) Aldehydes.- b) Ketones.- 10. Aliphatic polyhalides.- a) Polyhalides not containing fluorine.- b) Polyfluoroalkyl iodides.- c) Photoaddition of polyhalides to conjugated systems.- 11. Organophosphorus compounds.- a) Phosphines.- b) Phosphonates.- 12. Organosilicon compounds.- a) Trichlorosilane.- b) Organosilicon compounds.- 13. Organogermanium compounds.- References.- 18 Photochemical addition reactions of 1,4- and 1,2-quinones with alkylbenzenes or with ethers.- 1. Addition of chloranil to hydrocarbons.- 2. Addition of phenanthrenequinone to hydrocarbons.- 3. Addition of phenanthrenequinone or tetrachloro-o-quinone to ethers 184 References.- 19 Photochemical additions of aldehydes to quinones, quinone imines and quinone oximes.- 1. Addition of aldehydes to 1,2-quinones.- 2. Addition of aldehydes to 1,4-quinones.,.- 3. Addition of aldehydes to quinone imines and quinone oximes.- a) Quinone imines.- b) Quinone oximes.- References.- 20 Photoreductions with the aid of alcohols, ethers and other hydrogen donors.- 1. Photoreductions of C=C bonds.- 2. Photoreductions of C=O bonds. Formation of benzhydrols.- 3. Photoreductions of C=N bonds.- 4. Photoreductions of gem. chloronitroso compounds. Formation of oximes.- References.- 21 Formation of carbinols by photochemical addition of ketones and aldehydes to methylene groups.- 1. Addition of ketones.- 2. Addition of aldehydes.- References.- 22 Photochemical formation and photolysis of 1,2-ethanediols.- 1. Formation of 1,2-ethanediols by the addition of alcohols to ketones.- 2. Formation of 1,2-ethanediols via reductive dimerization.- a) Aldehydes.- b) Monoketones.- c) 1,2,3-Triketones.- d) ?-Ketocarboxylic acids and o-acylbenzoic acids.- 3. Photochemical cleavage of 1,2-ethanediols by carbonyl compounds 211 References.- 23 Photochemistry of deoxybenzoin derivatives.- Photochemistry of deoxybenzoin derivatives.- References.- 24 Photochemical decarbonylation.- 1. Decarbonylation of ketones.- a) Saturated cyclic ketones.- b) Unsaturated cyclic ketones.- c) Aromatic ketones.- 2. Decarbonylation of a ketene.- 3. Decarbonylation of aldehydes.- 4. Decarbonylation of S-acyl xanthates.- References.- 25 Photochemical formation and reactions of carboxylic acids and their derivatives.- 1. Formation of aliphatic carboxylic acids by the action of oxygen and water on alkyl halides.- 2. Formation of carboxylic acids by photolysis of cyclic ketones.- a) Saturated ketones.- b) Unsaturated ketones.- 3. Formation of acid derivatives.- a) Amides.- b) Lactones.- c) Acyl chlorides.- 4. Photochemical reactions of esters involving the acyloxy groups.- a) Rearrangements of esters.- b) Reductive elimination of an acetoxy group.- c) Light-induced Fries rearrangement.- 5. Further formation modes of esters.- a) Formation of ?-ketocarboxylates from ?-keto acetais.- b) Formation of esters from 2-butene-l,4-diones.- c) Formation of an ester from a diflavylene compound.- 6. Formation of fluorenecarboxylic acids by photolysis of fluoranthenols 239 References.- 26 Photochemical reactions with N-halogenated amines.- 1. Photochemical replacement of chlorine in N-chloroamines by hydrogen.- 2. The light-induced Hofmann-Löffler reaction.- a) Synthesis of pyrrolidines.- b) Synthesis of bridged nitrogen compounds.- c) Synthesis of conanines.- d) Synthesis of pyrrolidines.- 3. Formation of chloroalkylamines from N-chloroamines.- a) N-Butyl-4-chlorobutylamine.- b) Molecular rearrangements of steroidal N-chloroamines.- References.- 27 Photochemical transformations of organic nitrites.- 1. Photochemical reactions of nitrites involving fission of oxygen-nitrogen bonds..- The Barton reaction.- a) Simple aliphatic and alicyclic nitrites.- b) Epimerization in nitrite photolysis.- c) Steroidal nitrites.- 2. Photochemical reactions of nitrites involving fission of carbon-carbon bonds..- a) Syntheses of nitrosoalkanes.- b) Hydroxamic acids.- c) Fragmentation reactions in the steroid series.- References.- 28 Photochemical dealkylation of nitrogen compounds.- 1. Photolysis of N-alkyl and N-aralkyl amines.- 2. Photolysis of N-alkyl nitrogen heterocycles.- References.- 29 Photochemical introduction of cyano and nitroso groups.- 1. Formation of nitriles.- 2. Formation of geminai chloronitroso and dimeric nitroso compounds.- 3. Formation of diphenylfuroxan via ?-chloro-a-nitrosotoluene.- 4. Formation of oximes from hydrocarbons through photolysis of NOCI or NO/Cl2 mixtures.- a) Photolysis of NOCI.- b) Photolysis of NOCI in the presence of HCl or NO.- c) Photolysis of NO, Cl2 and HCl.- References.- 30 Photochemical transformations of unsaturated nitro compounds.- 1. Photolysis reactions of unsaturated nitro compounds.- 2. Photochemical conversion of aromatic nitro compounds to nitroso compounds.- 3. Photoreduction of an aromatic nitro compound to an aniline derivative.- 4. Photocyclization reactions of aromatic nitro compounds.- References.- 31 Light-induced reactions of diazoalkanes, diazirines and related compounds.- 1. Photoaddition reactions of carbenes to unsaturated systems resulting in ring formation.- a) Formation of cyclopropane compounds.- b) Formation of oxide rings.- c) Formation of aziridine rings.- d) Formation of cyclopropene compounds.- 2. Photoaddition reactions of carbenes to saturated compounds resulting in insertion into sigma bonds.- a) Insertion into C—C, C—O and C-halogen bonds.- b) Insertion into C—H bonds.- c) Insertion into O—H bonds.- d) Insertion into N—H bonds.- 3. Photodimerization reactions of carbenes.- 4. Miscellaneous photochemical reactions of carbenes.- a) Isomerization reactions with formation of olefins.- b) Univalent hydrogenation with subsequent dimerization.- c) Addition to oxygen.- 5. Photolysis of diazirines.- 6. Addition of diazomethane to olefins with formation of a pyrazoline 292 References.- 32 Photochemical syntheses with diazoketones, quinone diazides and iminoquinone diazides.- 1. Acyclic mono-diazoketones.- a) Conversion to ketenes and ?, ?-unsaturated ketones.- b) Photolysis in the presence of water or alcohol.- c) Photolysis in the presence of N-methylaniline and ethanethiol.- d) Photolysis in the presence of azo compounds.- e) Photolysis in the presence of azomethines.- f) Replacement of the diazo group by hydrogen.- g) Intramolecular addition of a carbene.- 2. Acyclic bis-diazoketones.- 3. Cyclic ?-diazoketones.- a) Ring contraction of five-membered rings.- b) Ring contraction of six-membered ring systems.- c) Ring contraction of o-quinone diazides (Süs reaction).- d) Photolysis of cyclic a-diazoketones not leading to ring contraction.- 4. Azo dyes from quinone diazides.- 5. p-Quinone diazides and p-iminoquinone diazides.- References.- 33 Photochemical syntheses with diazonium salts and diazosulfonates.- 1. Reductive deamination of diazonium salts.- 2. Replacement of the diazonium group by halogen or the hydroxy group.- 3. Photolysis of diazonium salts as a method of cyclization.- 4. Change in reactivity of aryl diazosulfonates.- 5. Photolysis of a 1,2,3-thiadiazine S,S-dioxide.- References.- 34 Synthetic applications of light-induced reactions of azides.- 1. Photolysis of alkyl azides.- 2. Photolysis of aryl azides.- a) Carbazoles and 4-phenylbenzofuroxan from 2-azidobiphenyl derivatives.- b) Photochemical conversion of aryl azides to azo compounds.- 3. Photolysis of acyl azides.- a) The light-induced Curtius rearrangement.- b) Formation of lactams.- c) Formation of amides.- 4. Photochemical reaction of ethyl azidoformate.- a) Reaction with cyclic hydrocarbons.- b) Reaction with alcohols.- 5. Photochemical syntheses with sulfonic acid azides.- a) Photolysis in methanol.- b) Photolysis in sulfoxides.- c) Photolysis in sulfides.- References.- 35 Photolysis of pyrazolines, pyrazoles, azo compounds, 1,2,3-thiadiazoles, and p-benzoquinone diimine N,N?-dioxides.- 1. Photolysis of pyrazolines.- 2. Photolysis of pyrazoles.- 3. Photolysis of diaroyl azo compounds.- 4. Photolysis of 1,2,3-thiadiazoles.- 5. Photolysis of p-benzoquinone diimine N,N’-dioxides.- References.- 36 Miscellaneous light-induced reactions of organic nitrogen compounds.- 1. Incorporation of C1 or C2 fragments by the photochemical reaction of various nitrogen compounds with alcohols.- a) Benzo[f]quinolines from Schiff’s bases.- b) Imidazolidines from diamines or from Schiff s bases.- c) Oxazolidines from Schiff’s bases.- 2. Photolysis of oxadiazolinones.- 3. Light-induced abnormal benzidine rearrangement.- 4. Light-induced condensations involving primary amines and aldehydes.- 5. Aromatic nitriles by photochemical cleavage of aromatic aldazines 339 References.- 37 Photohalogenation.- 1. Photohalogenation. Scope of the reaction.- 2. Photochlorination.- a) Chlorination of benzene in the presence of iodine.- b) Chlorination of benzene in the presence of maleic anhydride.- c) Replacement of the sulfonyl chloride group by chlorine.- d) Replacement of the nitroso group by chlorine.- e) Replacement of alkyl groups by chlorine.- f) Solvent effects on the site of attack by chlorine.- g) Chlorination of a cyclic trisulfone.- 3. Photobromination.- a) Migration of alkyl groups during bromination.- b) Bromination in the presence of oxygen.- c) Bromination in the allylic position with the aid of bromine.- d) Bromination with chlorine-bromine mixtures.- e) Orienting effects in the photobromination of alkyl bromides.- f) Bromination of aryl selenocyanates.- 4. Photoiodination.- 5. Photohalogenation with the aid of inorganic and organic halides.- a) Experiments with iodine chloride.- b) Chlorination with sulfuryl chloride.- c) Chlorination with trichloromethanesulfonyl chloride.- d) Chlorination with trichloromethanesulfenyl chloride.- e) Chlorination and bromination with the aid of N-chloro- and N-bromo-succinimide.- f) Bromination with the aid of dibromodimethylhydantoin.- References.- 38 Photochemical conversions of organic halides.- 1. Replacement of bromine by hydrogen, chlorine or 82Br.- a) Replacement of bromine by hydrogen.- b) Replacement of bromine by chlorine or 82Br.- 2. Replacement of iodine in iodides by hydrogen, nitric oxide or chlorine.- a) Experiments with aliphatic iodides.- b) Chlorobenzene from iodobenzene by photochemical decomposition of iodine chloride.- 3. Deiodination of aliphatic iodides.- 4. Debromination of l,l-diaryl-2-bromoethylenes.- 5. Formation of organomercury compounds by the action of mercury on alkyl iodides.- 6. Preparation of hexaarylethanes by the action of triarylmethyl halides on tri-arylmethanes.- 7. Photolysis of aromatic iodo compounds.- a) Iodobenzene and related substances.- b) Formation of benzyne on photolysis of 1,2-diiodobenzene or (2-iodophenyl)-mercury iodide.- 8. Photolysis of alkyl hypoiodites, acyl hypoiodites and N-iodoamides.- a) Photolysis of alkyl hypoiodites. Preparation of ethers.- b) Photolysis of acyl hypoiodites. Replacement of the carboxyl group by iodine.- c) Photolysis of N-iodoamides. Preparation of lactones.- References.- 39 Photochemical formation of hydroperoxides and peroxides.- 1. Replacement of hydrogen by the hydroperoxide group.- a) Unsensitized photooxidation of unsaturated compounds.- b) Photosensitized oxidation of olefins.- c) Photosensitized oxidation of secondary alcohols.- d) Photooxidation of ethers.- e) Photooxidation of nitrogen compounds.- f) Photooxidation of a phenol.- 2. Transannular peroxides from cyclic 1,3-dienes.- a) Epidioxides from alicyclic 1,3-dienes.- b) Epidioxides from fused 1,3-cyclohexadienes.- e) Epidioxides from acenes.- d) Photooxidation of carbo- and heterocyclic cyclopentadienes.- 3. Photochemical formation of bis-aralkyl and bis-acyl peroxides.- a) Formation of six-membered cyclic peroxides.- b) Formation of open chain peroxides.- c) Formation of acyl peroxides.- 4. Miscellaneous photochemical oxidation reactions.- a) Oxidative cleavage of C—C bonds.- b) Photooxidation of Curare alkaloids.- References.- 40 Photochemical formation and transformations of epoxides.- 1. Photochemical formation of epoxides.- 2. Photoisomerization of epoxyketones.- a) Acyclic ?, ?-epoxyketones.- b) Acyclic ?, ?-epoxyketones.- c) Cyclic ?, ?-epoxyketones.- d) Steroid ?, ?-epoxy ketones.- References.- 41 Photochemical formation of four membered rings with one oxygen atom (Paternò-Büchi reaction).- 1. Formation of oxetanes.- a) Cycloaddition of aldehydes or ketones to olefins.- b) Intramolecular cycloaddition leading to oxetanes.- c) Cycloaddition of p-quinones to olefins leading to spirooxetanes.- d) Cycloaddition of 1,2-dicarbonyl compounds to olefins leading to ?-keto-oxtanes.- e) Formation of oxetanes bearing functional groups.- 2. Formation of oxetes as intermediates in the cycloaddition of carbonyl compounds to acetylenes.- 3. Cycloaddition of p-benzoquinone to conjugated dienes not resulting in formation of oxetanes.- References.- 42 Photochemical formation and reactions of furans.- 1. Photoisomerization of quinoid compounds to furan derivatives.- 2. Photochemical reactions of furans with oxygen.- a) Simple furan derivatives.- b) Fused furan systems.- c) Aryl furans.- d) [2.2](2,5)Furanophane.- 3. Photoaddition of methanol to a furan derivative.- References.- 43 Photochemical formation and transformations of organic sulfur compounds.- 1. Photochemical syntheses using SO2, SO2C12 and SC12.- a) Sulfochlorination.- b) Sulfenylchlorination.- c) Sulfoxidation.- d) Cyclic sulfates from sulfur dioxide and o-quinones.- 2. Photochemical formation and transformations of sulfides.- a) Thioethers from di- and trisulfides.- b) Photolysis of 9,9,-bis-(phenylthio)-9,9/-bifluorene.- c) Insertion reaction of mercury with disulfides.- d) Conversion of a disulfide to a sulfenyl chloride.- e) Action of mercaptoacetic acid on benzo[a]pyrene.- f) Photolysis of a dixanthate.- 3. Photochemical thiocyanation.- 4. Photooxidation.- a) Sulfoxides.- b) Thiourea.- c) Conversion of thioketones into ketones.- d) Co-oxidation of thiols and olefins by oxygen.- 5. Miscellaneous photochemical reactions of sulfur compounds.- a) Photolysis of sulfones.- b) Photolysis of unsaturated sultones.- c) Photolysis of thiobenzophenone in the presence of olefins.- d) Photochemical formation of a dipyridyl sulfide from a 1,4-dihydropyridine-thione.- e) Photochemical reactions involving extrusion of sulfur from dithietanes and thiiranes.- f) Photochemical aryl migration in arylthiophenes.- References.- 44 Photochemical reactions of organophosphorus and organoarsenic compounds.- 1. Organophosphorus compounds.- a) Light-induced addition of dialkyl phosphonates to quinines.- b) Photochemical reactions of trialkyl phosphites.- c) Photolysis of triarylphosphines.- d) Photochemical synthesis of phosphonium salts.- e) Photolysis of tetraarylphosphonium salts.- 2. Organoarsenic compounds.- References.- 45 Photochemical formation and reactions of organometallic compounds.- 1. Light-induced formation of organometallic carbonyl compounds from metal carbonyls and organic compounds.- 2. Photochemical reactions of organometallic carbonyl compounds.- a) Substitution reactions with electron donors.- b) Photochemical decarbonylation of organometallic acyl derivatives to alkyl derivatives.- 3. Photochemical reactions of organo tin compounds.- a) Light-induced reaction of hexamethylditin with trifluoroiodomethane.- b) Synthesis of 1,2,3-triphenylazulene by photolysis of an organotin compound.- c) Photosensitized oxygenation of organotin compounds.- 4. Photochemical reactions of organomercury compounds.- a) Photolysis reactions with formation of arylmercury halides.- b) Photolysis reactions with formation of mercury.- 5. Miscellaneous photochemical reactions of organometallic compounds.- a) Light-induced formation of a Grignard reagent from an aliphatic bromide.- b) Photodimerization of a metal-complexed olefin.- c) Photolysis of aromatic lithium compounds.- d) Photolysis of iron pentacarbonyl in nitrobenzene solution.- References.- 46 Light sources and light filters in preparative organic photochemistry.- 1. Light sources.- a) Low-pressure sodium vapor lamps.- b) High-pressure sodium vapor lamps.- c) Low-pressure mercury lamps.- d) High-pressure mercury lamps.- e) Super-high-pressure mercury lamps.- f) Super-high-pressure xenon-mercury lamps.- g) High-pressure xenon lamps.- h) Sunlight.- i) Incandescent lamps.- j) Halogen incandescent lamps.- k) Fluorescent tubes.- 1) Vortex-stabilized plasma lamps.- m) Low-pressure gas discharge lamps for the far UV.- n) Flash lamps.- o) Lasers.- Tables.- 2. Light filters.- a) Solid filter materials.- b) Liquid filters.- c) Interference filters.- d) Reflection interference filters.- References.- A selective bibliography on photochemistry.- Author Index.- Reaction Index.- Sensitizer Index •.- Compound Index.