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Recent Reviews 126. Remers, W. A. Indole Aldehydes and Ketones, p 357.
135. Kearns, D. R. Solvent and Solvent Isotope Effects on
Marine Natural Products, Chemical and Biological Perspectives (Vol. 2, P. J. Scheuer, Ed,), Academic Press: New York, 1978
136. Foote, C. S. Quenching of Singlet Oxygen. 137. Schaap, A. P.; Zaklika, K. A. 1,2-CycloadditionReactions
the Lifetime of Singlet Oxygen. of Singlet Oxygen. 138. Bartlett, P. D.; Landis, M. E. The 1,2-Dioxetanes. 139. Gollnick, K.; Kuhn, H. J. Ene-Reactions with Singlet
127. Liaaen-Jensen, S. Marine Carotenoids. 128. Goad, L. J . The Sterols of Marine Invertebrates:
Oxygen.
Composition, Biosynthesis, and Metabolites. 129. Fenical, W. Diterpenoids. 130. Tursch, B.; Braekman, J. C.; Daloze, D.; Kaisin, M. Terpenoids from Coelenterates. 131. Sims, J. J.; Rose, A. F.; Izac, R. R. Applications of 13C NMR to Marine Natural Products.
140. Wasserman, H. W.; Lipshutz, B. H. Reactions of Singlet
Singlet Oxygen (H. H. Wasserman and R. W. Murray, Eds.), Academic Press: New York, 1979
Topics in Current Chemistry Springer Verlag: New York, 1979
132. Kasha, M.; Brabham, D. E. Singlet Oxygen Electronic
144. Houk, K. N. Theoretical and Experimental Insights Into Cycloaddition Reactions. 1979, 79, 1. 145. Paquette, L. A. The Development of Polyquinane Chemistry. 1979, 79, 41.
Oxygen with Heterocyclic Systems. 141. Saito, I.; Matsuura, T. The Oxidations of Electron-Rich
Aromatic Compounds. 142. Kaplan, M. L.; Trozzolo, A. M. Role of Singlet Oxygen in the Degradation of Polymers. 143. Krinsky, N. I. Biological Roles of Singlet Oxygen.
Structure and Photosensitization. 133. Ogryzlo, E. A. Gaseous Singlet Oxygen. 134. Murray, R. W. Chemical Sources of Singlet Oxygen.
Monographs science: New York, 1979.
146. Bohme, H.; Viehe, H. G., Eds. Iminium Salts in Organic
Chemistry, Part 2; Wiley-Interscience: New York, 1979. 147. Brown, G. H.; Wolken, J. J. Liquid Crystals and Biological Structures; Academic Press: New York, 1979. 148. Charney, E. The Molecular Basis of Optical Activity; Wiley-Interscience: New York, 1979. 149. Cheeseman, G. W. H.; Cookson, R. F., Eds. Condensed Pyrazine (Chemistry of Heterocyclic Compounds Series, Vol. 35); Wiley-Interscience: New York, 1979. 150. Dale, J. Stereochemistry and Conformational Analysis; Verlag Chemie International Inc.: New York, 1978. 151. Dalton, D. R. The Alkaloids: The Fundamental Chemistry-A Biogenetic Approach (Studies in Organic Chemistry Series, Vol. 7); Marcel Dekker: New York, 1979. 152. Dolphin, D., Ed, The Porphyrins, Vol. 111, Physical Chemistry, Part A; Academic Press: New York, 1978. 153. Dolphin, D., Ed. The Porphyrins, Vol. IV, Chemical Chemistry, Part B; Academic Press: New York, 1979. 154. Dunitz, J. D. X-Ray Analysis and the Structure of Organic Molecules; Cornel1 University Press: Ithaca, N.Y., 1979. 155. Engelhardt, H. (translated from German by G. Gutnikov). High Performance Liquid Chromatography; Springer-Verlag: New York, 1979. 156. Hansch, C.; Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology; Wiley-Inter-
157. Houghton, R. P. Metal Complexes in Organic Chemistry;
Cambridge University Press: Cambridge, 1979. 158. Kochi, J. K. Organic Mechanisms and Catalysis; Ac-
ademic Press: New York, 1978. 159. Levy, G. C.; Lichter, R. L. Nitrogen-15 Nuclear Magnetic
Resonance Spectroscopy; Wiley-Interscience: New York, 1979. 160. Metzger, J. V. Thiazole and Its Derivatives (Chemistry of Heterocyclic Compounds Series, Vol. 34, Parts 1 , 2 , and 3); Wiley-Interscience: New York, 1979. 161. Nonhebel, D. C.; Tedder, J. M.; Walton, J. C. Radicals; Cambridge University Press: Cambridge, 1979. 162. Patai, S., Ed. Chemistry of the Carbon-Carbon Triple Bond, Parts 1 and 2; Wiley-Interscience: New York, 1979. 163. Reichardt, Chr. Solvent Effects in Organic Chemistry: Monographs in Modern Chemistry Vol. 3; Verlag-Chemie: New York, 1979. 164. Remers, W. A. The Chemistry of Antitumor Antibiotics, Vol. 1; Wiley-Interscience: New York, 1979. 165. Shamma, M.; Hindenlang, D. M. Carbon-NMR Shift Assignments of Amines and Alkaloids; Plenum Press: New York, 1979. 166. Stowell, J. C. Carbanions in Organic Synthesis; Wiley-Interscience: New York, 1979.
Index Acetylenes, 162 Acetylene decarboxylic esters, reacns with heterocycles, 28 Alanes, alkenyl, 119 Aldehydes, Schmidt reacn of, 92 Aldol reaction, 122 A1 ha effect, 76 Alf:aloids, 105-109, 151 I3C NMR, 165 Alkene diazonium salts, 52 Alkylation, of enolates, 123 Anchimeric assistance, in homolysis, 49 Anils, condensation reacns of, 27 Anions, aryl, steric strain, 113 photoexcited states, 60 Annulenes, 50 hetero-, 25 Anthranilic acid alkaloids, 106
Antibiotics, antitumor, 164 orthosomycins, 104 Aromatic compounds, heterocyclic, 47, 67 oxidative coupling, 77 CY complexes, 91 singlet oxy en reacns, 141 Aspidosperma afkaloids, 107 Azides, 12 Bicyclo[3.3.l]nonanes, synth, 98 Biogenesis, alkaloids, 151 Biosynthesis, building blocks in, 55 -prophyrin, 2 Boranes, 44 alkenyl, 119 chiral allenic, 118 in isotopic labelling, 117 Butadiene, codimerization with ethylene, 35 Carbanions, 166
Carbohydrates, blood group, 61 as chiral templates, 16 glycosiduronic acids, 22 Carbonylation, of methanol, 34 Carcinogenicity, of tobacco nitrosamines, 9 Carotenoids, marine, 127 Catalysis, and mechanism, 158 by organometallic cmpds, 29-38 in propylene oxdn, 20 rearrangements in, 21 transition metal, 21 triphase, 54 Cations, isolated, 57 theoretical studies. 72 Cembranes, natural occ, 68 Chiral crystals in synthesis, 17 Chiral templates, carbohydrates as, 16 Cholinesterase inhibition, 84
Recent Reviews
4020 J. Org. Chem., Vol. 44, No. 22, 1979 Chromatography, liquid, 155 Complexes, metal, 157 riobium and tantalum, 10 transition metal in hydrogenation, 36 Conformational equilibria, in ESR, 112 Copper induced oxygenolysis, 114 Crystallo raphy, 154 Cycloadcfition, 1,3-dipolar, phosphorus cmpds, 80 singlet oxygen, 137 theory, 144 Cycloadditions, of acetylenecarboxylates, 28 Cyclopropanes, electrophilic in synth, 7 Cyclotrimerization, cyano cmpds, 89 Diazonium compounds, alkene-, 52 Dioxetanes, 1,2-, 138 Dipolar cyclization, 59 Diterpene alkaloids, synth, 105 Diterpenoids, marine, 129 Electrical conduction, organic solids, 42 Ene reactions, singlet oxygen, 139 Enolates, alkylation, 123 ESR, conformational equilibria in, 112 Esters, macrocyclic, 58 Fatty acids, unsaturated, oxidation, 63 Fischer-Tropsch reaction, 30 Glycosiduromic acids, 22 Heteroannulenes, p-excess, 25 Heterocycles, amination, 90 aroma cmpds, 67 N-contng, reacns with acetylenes, 28 by 1,5cyclization. 59 pyrazines, 149 singlet oxygen reams, 140 thiazole, 160 Heterocyclopolyaromatjic compounds, 47 Hexamethylenetetramine in synth, 96 Homolvsis. anchimericallv assisted, 49 HPLC,' 156 Hydride reduction, 100 101, 116 Hydroformylation, 29 Hvdroaenation, transition metal complexes in, 36 Hydrosilation, catal by transition metal, 37 Imidophosphorus compounds, rearr, 85 Iminium salts, 146 3-chloro-2-propen., 97 Indoles, 125-126 Indolizines, 26 Insecticides, pyrethroid, 62 Iron carbonyl, polybromoketone complex, 6 Isonitriles, 4 Liquid crystals, 147 Linear free energy, solvent polarity in, 48 Macr ocycles, 1,5,9-cyclododecatriene , 88 Macrocyclic esters, 58 Marine natural products, 127-131 of elimination reacns, 18 Mechanism, halogenation, 39 nitration and nitrosation, 39 solvent effects in, 5 solvent polarity in, 48 solvolysis, '110 Mechanisms, and catalysis, 158 Mercury cmpds, in synth, 120 Methanol, carbonylation of, 34 Methyl transfer reacns, 41 Micelles, structure of, 11 Monoterpene alkaloid glycosides, 109 Nickel, catalysis, 121 Nickel catalyzed olefin oligomerization, 31
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Niobium, alkylidene complexes, 10 Nitration, mechanism, 39 Nitriles, cyclotrimerization, 89 Nitrosamines, tobacco specific, 9 Nitrosation, mechanism, 39 NMR, 13C, alkaloids, 165 I3C marine natural products, 131 13C in nat products, 66 15N, 159 of optical isomers in soln, 82 relaxation studies, 43 Nucleofugality in elimination reacns, 18 Nucleophilic substitution, a-effect in, 76 arom, 91 photochemical, 70 Nucleotides, phosphorthioate analogues, 19 poly, synth, 23 Olefins, codimerization with butadiene, 35 metathesis, 38 Optical activity, origin, 148 Orbital symmetry, 53 Organic metals, 8, 42 Organometallic cmpds, 29-38 see indiv elements Orthosomycins, 104 1,3-0xazines,24 Oxidation, polyunsaturated fatty acids, 63 selective, of propylene, 20 Oxidative coupling, aromatic cmpds, 77 Oxygen, singlet, 132-143 Oxygenolysis, copper catalyzed, 114 Palladium catalyzed reactions, 14, 15, 32 Palladium com ounds, in synth, 120, 121 Papaveraceae aykaloids, 108 Peptides, 1 Pharmacolo ical activity, correlation, 156 Phase transfer catalysis, 54 Phosphinylidene cmpds, 83 Phosphorothioate analogues of nucleotides, 19 Phosphorus compounds, addn reacns, 95 as cholinesterase inhibitors, 84 in cycloaddn, 80 four-coordinate, 87 imide-amine rearrs, 85 monothiopyrophosphates, 81 with P-P bonds, 86 ylides, 124 Phosphorus pentachloride, reacns, 78 in condensed monolayers, 56 Photochemistry, donor-acceptor complexes, 73 of organic anions, 60 transition metal, 71 Photolysis, vacuum UV, 75 Photosensitization, singlet oxygen, 132 Photosensitized reacns, cadmium, 69 Photosubstitution, aromatic, 70 Polymer, arylene sulfide, 93 immobilizing media, 65 poly(iminomethylene), 4 reactivity of, 64 singlet oxygen degradation, 142 Polyquinanes, 145 Porph rins, 2, 152-153 Propygne, catal oxidn of, 20 Pyrethroids, synthetic, 62 Pyrazines, condensed, 149 Pyridines, Chichibabin reacn, 90 Quinacenes, 145 Radicals, 46, 161
additive reacns, 40 in photolysis, 75 verdazyl, 79 Rearrangements, u-T in catalysis, 21 Reduction, with group IV-VIB metals, 94 hydride, 101, 116 Reductions, ketone, with hydrides, 100 Rhodium catalysts, 34 Rhodium compounds, in synth, 120 Schmidt reaction, 92 Selenium compounds, 3 Singlet oxygen-see oxygen Solid phase reagents, 99, 102 Solvent effects, 163 initial and transition state, 5 Solvolytic reactions, electron demand in, 110 Spin delocalization, CF3 group, 111 Spin trapping, 46 Stereochemistry, 150 ketone reduction, 100 optical activity, 148 optical isomers and NMR, 82 tetraalkyl tin cleavage, 115 Steric strain, aryl anions and amines, 113 Steroids, C-nor-D-homo, 103 Sterols, marine, 128 Stilbene exciplexes, 15 Substituent constants. correlation analysis, 156 Sulfur cm ds, polyarylene sulfides, 93 Supportefrea ents, in synth, 65, 99 Surfactants, pghotochemistry in condensed layers, 57 Synthesis, aldol condensation in, 122 asymmetric via chiral crystals, 17 bicyclo[3.3.11 nonanes , 98 bromoketone-iron carbonyls in, 6 carbanions in, 166 88 with 1,5,9-~yclododecatriene, cyclopropanes in, 7 hexamethylenetetramine in, 96 iminium salts in, 146 natl prod using carbohydrates, 16 with organonickel complexes, 33 palladium-catalyzed, 14 polynucleotides, 23 reactivity umpolung, 51 using selenium cmpds, 3 supported reagents in, 99 trialkylborohydrides in, 45 Tantalum, alkylidene complexes, 10 Terpenoids, coelenterate, 130 Tetracyanoquinodimethanesalts, metallic, 8 Thiazole and derivatives, 160 Thiirenium ions, 74 Tin compounds, bromine cleavage, 115 Tobacco nitrosamines. 9 Trialkylborohydrides, in synthesis, 45 Triazines, by cyclotrimerization, 89 Trifluoromethyl groups, charge and spin delocalization, 111 Troponoid chemistry, 13 Umpolung, 51 Verdazyl radicals, 79 X-Ray crystallography, organic, 154 Ylids, phosphonium, reacns, 124 Zwittazido cleavage, 12
