Developments in the photochemistry of diazo compounds

Current Organic Chemistry

Volumn 13, Issue 7, 2009, Pages 763-787

  Candeias, Nuno R ^a   Afonso, Carlos A M ^a  

^a INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ABSTRACTING; CARBONYL COMPOUNDS; HYDROGEN;

CARBENES; CYCLOPROPANATION; DIAZO CARBONYL COMPOUNDS; DIAZO COMPOUNDS; HYDROGEN ABSTRACTION; HYDROGEN REACTION; ORGANICS; PHOTOLYTIC REACTIONS; SYNTHETIC APPLICATION; WOLFF REARRANGEMENT;

MOLECULAR OXYGEN;

EID: 69249087759     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527209788167231     Document Type: Review

References (147)

1. Wee, A.G.H. Rhodium(II)-catalyzed reaction of diazocompounds in the service of organic synthesis of natural and non-natural products. Curr. Org. Synth., 2006, 3, 499-555.
2. Davies, H.M.L.; Loe, O. Intermolecular C-H insertions of donor/ acceptor-substituted rhodium carbenoids: a practical solution for catalytic enantioselective C-H activation. Synthesis, 2004, 16, 2595-2608.
3. Ye, T.; McKervey, M.A. Organic-synthesis with a-Diazocarbonyl compounds. Chem. Rev., 1994, 94, 1091-1160.
4. Gois, P.M.P.; Afonso, C.A.M. Stereo- and regiocontrol in the formation of lactams by rhodium-carbenoid C-H insertion of adiazoacetamides. Eur. J. Org. Chem., 2004, 18, 3773-3788.
5. Zhang, Z.; Wang, J. Recent studies on the reactions of adiazocarbonyl compounds. Tetrahedron, 2008, 64, 6577-6605.
6. Davies, H.M.L.; Nikolai, J. Catalytic and enantioselective allylic C-H activation with donor-acceptor-substituted carbenoids. Org. Biomol. Chem., 2005, 3, 4176-4187.
7. Padwa, A.; Hornbuckle, S.F. Ylide formation from the reaction of carbenes and carbenoids with heteroatom lone pairs. Chem. Rev., 1991, 91, 263-309.
8. Davies, H.M.L. Recent advances in catalytic enantioselective intermolecular C-H functionalization. Angew. Chem. Int. Edit., 2006, 45, 6422-6425.
9. Ferreira, V.F. Synthesis of heterocyclic compounds by carbenoid transfer reactions. Curr. Org. Chem., 2007, 11, 177-193.
10. Davies, H.M.L.; Hedley, S.J. Intermolecular reactions of electronrich heterocycles with copper and rhodium carbenoids. Chem. Soc. Rev., 2007, 36, 1109-1119.
11. Nakamura, I.; Yamamoto, Y. Transition-metal-catalyzed reactions in heterocyclic synthesis. Chem. Rev., 2004, 104, 2127-2198.
12. Davies, H.M.L.; Beckwith, R.E.J. Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion. Chem. Rev., 2003, 103, 2861-2903.
13. Merlic, C.A.; Zechman, A.L. Selectivity in rhodium(II) catalyzed reactions of diazo compounds: effects of catalyst electrophilicity, diazo substitution, and substrate substitution. From chemoselectivity to enantioselectivity. Synthesis, 2003, 8, 1137-1156.
14. Cheng, Y.; Meth-Cohn, O. Heterocycles derived from heteroatomsubstituted carbenes. Chem. Rev., 2004, 104, 2507-2530.
15. Im, C. Y.; Okuyama, T.; Sugimura, T. Stereoselective formation of a chiral ether by intramolecular O-H insertion reaction of a metal carbenoid generated from diazoacetoacetate. Eur. J. Org. Chem., 2008, 2008, 285-294.
16. Davies, J.R.; Kane, P.D.; Moody, C.J. N-H insertion reactions of rhodium carbenoids. Part 5: a convenient route to 1,3-azoles. Tetrahedron, 2004, 60, 3967-3977.
17. Bulugahapitiya, P.; Landais, Y.; Parra-Rapado, L.; Planchenault, D.; Weber, V. A stereospecific access to allylic systems using rhodium(II)-vinyl carbenoid insertion into Si-H, O-H, and N-H bonds. J. Org. Chem., 1997, 62, 1630-1641.
18. DeAngelis, A.; Panne, P.; Yap, G.P.A.; Fox, J.M. Rh-catalyzed formation of dioxolanes from a-alkyl diazoesters: diastereoselective cycloadditions of carbonyl ylides with selectivity over b-hydride elimination. J. Org. Chem., 2008, 73, 1435-1439.
19. Curtius, T. Ueber die einwirkung von salpetriger säure auf salzsauren glycocolläther. Ber. Dtsch. Chem. Ges., 1883, 16, 2230.
20. Linder, M.R.; Steurer, S.; Podlech, J. (S)-3-(tert-Butyloxycarbonylamino)-4-phenylbutanoic acid. Org. Synth., 2002, 79, 154.
21. Day, A.C.; Raymond, P.; Southam, R.M.; Whiting, M.C. Preparation of secondary aliphatic diazo-compounds from hydrazones. J. Chem. Soc. C Org., 1966, 4, 467-469.
22. Ferreira, V.F.; Pereira, L.O.R.; de Souza, M.; Cunha, A.C. a-diazo carbonyl compounds: an atractive estrategy in organic synthesis. Quim. Nova, 2001, 24, 540-553.
23. Wurz, R.P.; Charette, A.B. Transition metal-catalyzed cyclopropanation of alkenes in water: Catalyst efficiency and in situ generation of the diazo reagent. Org. Lett., 2002, 4, 4531-4533.
24. Myers, E.L.; Raines, R.T. A Phosphine-Mediated Conversion of Azides into Diazo Compounds. Angew. Chem. Int. Edit., 2009, 48(13), 2359-2363.
25. Jin, T.; Yamamoto, Y. An efficient, facile, and general synthesis of 1H-indazoles by 1,3-dipolar cycloaddition of arynes with diazomethane derivatives. Angew. Chem. Int. Edit., 2007, 46, 3323-3325.
26. Liu, Z.J.; Shi, F.; Martinez, P.D.G.; Raminelli, C.; Larock, R.C. Synthesis of indazoles by the 3+2 cycloaddition of diazo compounds with arynes and subsequent acyl migration. J. Org. Chem., 2008, 73, 219-226.
27. Qi, X.B.; Ready, J.M. Copper-promoted cycloaddition of diazocarbonyl compounds and acetylides. Angew. Chem. Int. Edit., 2007, 46, 3242-3244.
28. Bunse, M.; Jodicke, D.; Kirmse, W. Free radical pathways in the nitrous-acid deamination of a-aminonitriles. J. Chem. Soc. Chem. Commun., 1992, 1, 47-49.
29. Smith, M.B.; March, J. Advanced organic chemistry: reactions, mechanisms, and structure, 5th ed.; Wiley: New York, 2001.
30. Zollinger, H. Diazo chemistry II: aliphatic, inorganic, and organometallic compounds; VCH, Weinheim: New York, 1995.
31. Coyle, J. D. Introduction to organic photochemistry; Wiley: New York, 1986.
32. Fien, J.; Kirmse, W. Intramolecular reactivity of triplet carbonyl-carbenes. Angew. Chem. Int. Edit., 1998, 37, 2232-2234.
33. Pastor-Perez, L.; Wiebe, C.; Perez-Prieto, J.; Stiriba, S.E. A tetramethoxybenzophenone as efficient triplet photocatalyst for the transformation of diazo compounds. J. Org. Chem., 2007, 72, 1541-1544.
34. McKellar, A.R.W.; Bunker, P.R.; Sears, T.J.; Evenson, K.M.; Saykally, R.J.; Langhoff, S.R. Far infrared-laser magneticresonance of singlet methylene - singlet triplet perturbations, singlet triplet transitions, and the singlet triplet splitting. J. Chem. Phys., 1983, 79, 5251-5264.
35. Khodabandeh, S.; Carter, E.A. Methyl substitution in carbenes: lack of steric or hyperconjugative stabilization effects on the ethylidene singlet-triplet splitting. J. Phys. Chem., 1993, 97, 4360-4364.
36. Modarelli, D.A.; Morgan, S.; Platz, M.S. Carbene formation, hydrogen migration, and fluorescence in the excited states of dialkyldiazirines. J. Am. Chem. Soc., 1992, 114, 7034-7041.
37. Richards, C.A.; Kim, S.-J.; Yamaguchi, Y.; Schaefer, H.F. Dimethylcarbene: a singlet ground state? J. Am. Chem. Soc., 1995, 117, 10104-10107.
38. Matzinger, S.; Fulscher, M.P. Methyl substitution in carbenes - A theoretical prediction of the singlet-triplet energy separation of dimethylcarbene. J. Phys. Chem., 1995, 99, 10747-10751.
39. Irikura, K.K.; Goddard, W.A.; Beauchamp, J. L. Singlet-triplet gaps in substituted carbenes CXY (X, Y = H, fluoro, chloro, bromo, iodo, silyl). J. Am. Chem. Soc., 1992, 114, 48-51.
40. Bauschlicher, C.W.; Schaefer, H.F.; Bagus, P.S. Structure and energetics of simple carbenes methylene, fluoromethylene, chloromethylene, bromomethylene, difluoromethylene, and dichloromethylene. J. Am. Chem. Soc., 1977, 99, 7106-7110.
41. Harrison, J.F.; Liedtke, R.C.; Liebman, J.F. The multiplicity of substituted acyclic carbenes and related molecules. J. Am. Chem. Soc., 1979, 101, 7162-7168.
42. Bourissou, D.; Guerret, O.; Gabbai, F.P.; Bertrand, G. Stable carbenes. Chem. Rev., 2000, 100, 39-92.
43. Baird, N.C.; Taylor, K.F. Multiplicity of the ground state and magnitude of the T1-S0 gap in substituted carbenes. J. Am. Chem. Soc., 1978, 100, 1333-1338.
44. Hoffmann, R.; Zeiss, G.D.; Van Dine, G.W. The electronic structure of methylenes. J. Am. Chem. Soc., 1968, 90, 1485-1499.
45. Geise, C. M.; Hadad, C. M. Computational study of the electronic structure of substituted phenylcarbene in the gas phase. J. Org. Chem., 2000, 65, 8348-8356.
46. Wang, J.-L.; Toscano, J.P.; Platz, M.S.; Nikolaev, V.; Popik, V. Dicarbomethoxycarbene. A laser flash photolysis study. J. Am. Chem. Soc., 1995, 117, 5477-5483.
47. Lowry, T.H.; Richardson, K.S. Mechanism and theory in organic chemistry, 3rd ed.; Harper & Row: New York, 1987.
48. Tomioka, H.; Hirai, K.; Tabayashi, K.; Murata, S.; Izawa, Y.; Inagaki, S.; Okajima, T. Neighboring group participation in carbene chemistry - effect of neighboring carboxylate group on carbene reactivities. J. Am. Chem. Soc., 1990, 112, 7692-7702.
49. Scott, A.P.; Platz, M.S.; Radom, L. Singlet-triplet splittings and barriers to Wolff rearrangement for carbonyl carbenes. J. Am. Chem. Soc., 2001, 123, 6069-6076.
50. Von E. Doering, W.; Knox, L. H. Comparative reactivity of methylene, carbomethoxycarbene and bis-carboethoxycarbene toward the saturated carbon-hydrogen bond. J. Am. Chem. Soc., 1961, 83, 1989-1992.
51. Wang, Y.; Hadad, C.M.; Toscano, J.P. Solvent dependence of the 2-N aphthyl(carbomethoxy)carbene singlet-triplet energy gap. J. Am. Chem. Soc., 2002, 124, 1761-1767.
52. Geise, C.M.; Wang, Y.; Mykhaylova, O.; Frink, B.T.; Toscano, J. P.; Hadad, C. M. Computational and experimental studies of the effect of substituents on the singlet-triplet energy gap in Phenyl(carbomethoxy) carbene. J. Org. Chem., 2002, 67, 3079-3088.
53. Langan, J.G.; Sitzmann, E.V.; Eisenthal, K.B. Picosecond laser studies on the effect of structure and environment on intersystem crossing in aromatic carbenes. Chem. Phys. Lett., 1984, 110, 521-527.
54. Sitzmann, E.V.; Langan, J.; Eisenthal, K.B. Intermolecular effects on intersystem crossing studied on the picosecond timescale: the solvent polarity effect on the rate of singlet-to-triplet intersystem crossing of diphenylcarbene. J. Am. Chem. Soc., 1984, 106, 1868-1869.
55. Wypych, G. Handbook of solvents; ChemTec: Toronto, 2001.
56. Tomioka, H.; Hirai, K. Effect of the phosphonate group on the reactivity of carbenes - neighboring phosphonate group participation. J. Chem. Soc. Chem. Commun., 1989, 6, 362-364.
57. Wright, B.B.; Platz, M.S. Chemistry and kinetics of aryl carbenes in methanol at low temperatures. J. Am. Chem. Soc., 1984, 106, 4175-4180.
58. Bodor, N.; Dewar, M.J.S.; Wasson, J.S. Ground states of molecules. XIX. Carbene and its reactions. J. Am. Chem. Soc., 1972, 94, 9095-9102.
59. Savino, T.G.; Kanakarajan, K.; Platz, M.S. Unusual temperature-dependent isotope effects in the reactions of phenylcarbene with cyclohexene and cyclohexane. J. Org. Chem., 1986, 51, 1305-1309.
60. Tomioka, H.; Itoh, M.; Yamakawa, S.; Izawa, Y. The reactivity of carbene from photolysis of diazo-compounds towards carbonhydrogen bonds - Effects of structure, temperature, and matrix on the insertion selectivity. J. Chem. Soc. Perkin Trans. 2, 1980, 4, 603-609.
61. Ganzer, G.A.; Sheridan, R.S.; Liu, M.T.H. Reaction of phenylchlorocarbene in oxygen-doped matrices. J. Am. Chem. Soc., 1986, 108, 1517-1520.
62. Fujiwara, Y.; Tanimoto, Y.; Itoh, M.; Hirai, K.; Tomioka, H. Laser flash-photolysis studies of methoxycarbonyl phenyl carbene and its derived carbonyl oxide at room-temperature. J. Am. Chem. Soc., 1987, 109, 1942-1946.
63. Chiang, Y.; Kresge, A.J.; Pruszynski, P.; Schepp, N.P.; Wirz, J. The mechanism of acylcarbene insertion into O-H bonds - direct observation of the enol of a carboxylic-acid ester in aqueoussolution. Angew. Chem. Int. Edit., 1991, 30, 1366-1368.
64. Wolff, L. Ueber Diazoanhydride. Justus Liebigs Ann. Chem., 1902, 325, 129-195.
65. Kirmse, W. 100 years of the Wolff rearrangement. Eur. J. Org. Chem., 2002, 14, 2193-2256.
66. Popik, V.V.; Nikolaev, V.A. Stereochemistry and thermal-stability of diazoketones. J. Chem. Soc. Perkin Trans. 2, 1993, 10, 1791-1793.
67. Bogdanova, A.; Popik, V.V. Experimental and theoretical investigation of reversible interconversion, thermal reactions, and wave-length-dependent photochemistry of diazo meldrum's acid and its diazirine isomer, 6,6-Dimethyl-5,7-dioxa-1,2-diaza-spiro[2,5]oct-1-ene-4,8-dione1. J. Am. Chem. Soc., 2003, 125, 14153-14162.
68. Bogdanova, A.; Popik, V.V. Experimental and theoretical analysis of the photochemistry and thermal reactivity of ethyl diazomalonate and its diazirino isomer. The role of molecular geometry in the decomposition of diazocarbonyl compounds. J. Am. Chem. Soc., 2004, 126, 11293-11302.
69. Toscano, J.P.; Platz, M.S.; Nikolaev, V.; Popic, V. Carboethoxy-carbene - A laser flash-photolysis study. J. Am. Chem. Soc., 1994, 116, 8146-8151.
70. Wang, J.L.; Likhotvorik, I.; Platz, M.S. A laser flash photolysis study of 2-Naphthyl(carbomethoxy)carbene. J. Am. Chem. Soc., 1999, 121, 2883-2890.
71. Wang, Y.H.; Yuzawa, T.; Hamaguchi, H.O.; Toscano, J.P. Time-resolved IR studies of 2-naphthyl(carbomethoxy)carbene: reactivity and direct experimental estimate of the singlet/triplet energy gap. J. Am. Chem. Soc., 1999, 121, 2875-2882.
72. Tomioka, H.; Okuno, H.; Izawa, Y. Mechanism of the photochemical Wolff rearrangement - the role of conformation in the photolysis of a-Diazo carbonyl-compounds. J. Org. Chem., 1980, 45, 5278-5283.
73. Roth, H.D.; Manion, M.L. Solution photochemistry of diazoacetone. Wolff rearrangement and acetylmethylene. J. Am. Chem. Soc., 1976, 98, 3392-3393.
74. Burdzinski, G.T.; Wang, J.; Gustafson, T.L.; Platz, M. S. Study of concerted and sequential photochemical Wolff rearrangement by femtosecond UV-vis and IR spectroscopy. J. Am. Chem. Soc., 2008, 130, 3746-3747.
75. Ortica, F.; Pohlers, G.; Scaiano, J.C.; Cameron, J.F.; Zampini, A. Laser flash photolysis of 2-diazo-1,3-diphenyl-1,3-propanedione: an unusual long-lived triplet as a reaction intermediate. Org. Lett., 2000, 2, 1357-1360.
76. McMahon, R.J.; Chapman, O.L.; Hayes, R.A.; Hess, T.C.; Krimmer, H. P. Mechanistic studies on the Wolff rearrangement: the chemistry and spectroscopy of some a-keto carbenes. J. Am. Chem. Soc., 1985, 107, 7597-7606.
77. Wang, J.; Burdzinski, G.; Kubicki, J.; Gustafson, T.L.; Platz, M.S. Ultrafast carbene - carbene isomerization. J. Am. Chem. Soc., 2008, 130, 5418-5419.
78. Wang, J.; Burdzinski, G.; Kubicki, J.; Platz, M. S. Ultrafast UVVis and IR studies of p-Biphenylyl acetyl and carbomethoxy carbenes. J. Am. Chem. Soc., 2008, 130, 11195-11209.
79. Kaplan, F.; Meloy, G.K. Structure of Diazoketones. A study of hindered internal rotation. J. Am. Chem. Soc., 1966, 88, 950-956.
80. Zeller, K.P.; Blocher, A.; Haiss, P. Oxirene participation in the photochemical Wolff rearrangement. Mini Rev. Org. Chem., 2004, 1, 291-308.
81. Haiss, P.; Zeller, K.P. The photochemical Wolff rearrangement of 3-diazo-1,1,1-trifluoro-2-oxopropane revisited. Org. Biomol. Chem., 2003, 1, 2556-2558.
82. Zeller, K.P.; Muller, E.; Meier, H. Studies on Wolff rearrangement. 2.Migration ability of hydrogen and mathyl and aryl groups. Tetrahedron, 1972, 28, 5831-5838.
83. Chaimovich, H.; Vaughan, R. J.; Westheimer, F. H. Rearrangement accompanying photolysis of diazoacyl esters. J. Am. Chem. Soc., 1968, 90, 4088-4093.
84. Dominh, T.; Strausz, O.P.; Gunning, H.E. Photochemistry of Diazo Esters. 2.a Novel Reaction Path. J. Am. Chem. Soc., 1969, 91, 1261-1263.
85. Strausz, O.P.; Dominh, T.; Gunning, H.E. Rearrangement and polar reaction of carbethoxymethylene in 2-Propanol. J. Am. Chem. Soc., 1968, 90, 1660-1661.
86. Tomioka, H.; Okuno, H.; Izawa, Y. Carbenes in a rigid matrix - substituent effects on the temperature-dependence of acarbonylcarbene reactions. J. Chem. Soc. Perkin Trans. 2, 1980, 11, 1636-1641.
87. Liao, M.; Dong, S.; Deng, G.; Wang, J. Synthesis of oxygen-containing heterocyclic compounds based on the intramolecular OH insertion and Wolff rearrangement of a-diazocarbonyl compounds. Tetrahedron Lett., 2006, 47, 4537-4540.
88. Tomioka, H.; Hayashi, N.; Sugiura, T.; Izawa, Y. Evidence for protonation of typically electrophilic carbenes by methanol. J. Chem. Soc. Chem. Commun., 1986, 17, 1364-1366.
89. Celebi, S.; Leyva, S.; Modarelli, D.A.; Platz, M.S. 1,2-Hydrogen migration and alkene formation in the photoexcited states of alkylphenyldiazomethanes. J. Am. Chem. Soc., 1993, 115, 8613-8620.
90. Shin, S.H.; Cizmeciyan, D.; Keating, A.E.; Khan, S.I.; Garcia-Garibay, M.A. control of carbene reactivity by crystals. A highly selective 1,2-H shift in the solid-to-solid reaction of 1-(4'-Biphenylyl)-2-phenyldiazopropane to (Z)-1-(4'-Biphenylyl)-2-phenylpropene. J. Am. Chem. Soc., 1997, 119, 1859-1868.
91. Garcia-Garibay, M.A. Reaction of arylcarbenes with methanol: triplet-state reactivity or spin-state equilibrium as a moving target? J. Am. Chem. Soc., 1993, 115, 7011-7012.
92. Wang, J.; Burdzinski, G.; Gustafson, T.L.; Platz, M.S. Ultrafast study of p-Biphenylyldiazomethane and p-Biphenylylcarbene. J. Org. Chem., 2006, 71, 6221-6228.
93. Wang, J.; Burdzinski, G.; Gustafson, T.L.; Platz, M.S. Ultrafast study of p-Biphenylyldiazoethane. The chemistry of the diazo excited state and the relaxed carbene. J. Am. Chem. Soc., 2007, 129, 2597-2606.
94. Sugiyama, M.H.; Celebi, S.; Platz, M.S. A significant barrier to 1,2-hydrogen migration in singlet 1-phenylethylidene. A laser flash photolysis study. J. Am. Chem. Soc., 1992, 114, 966-973.
95. Calvo-Losada, S.; Sordo, T.L.; Lopez-Herrera, F.J.; Quirante, J.J. The influence of protecting the hydroxyl group of b-oxy-a-diazo carbonyl compounds in the competition between Wolff rearrangement and 1,2-hydrogen shift. Density functional theory study and topological analysis of the charge density. Theor. Chem. Acc., 2000, 103, 423-430.
96. Calvo-Losada, S.; Suarez, D.; Sordo, T.L.; Quirante, J.J. Competition between Wolff rearrangement and 1,2-Hydrogen shift in b-Oxy-a-ketocarbenes: electrostatic and specific solvent effects. J. Phys. Chem. B, 1999, 103, 7145-7150.
97. Motschiedler, K.; Gudmundsdottir, A.; Toscano, J.P.; Platz, M.; Garcia-Garibay, M.A. Excited precursor reactivity, fast 1,2-H shifts, and diffusion-controlled methanol insertion in 1,2-Diphenylalkylidenes. J. Org. Chem., 1999, 64, 5139-5147.
98. Nickon, A. New perspectives on carbene rearrangements: migratory aptitudes, bystander assistance, and geminal efficiency. Acc. Chem. Res., 1993, 26, 84-89.
99. Moss, R.A. Dynamics of intramolecular carbenic rearrangements. Pure Appl. Chem., 1995, 6 7(5), 741-747.
100. Liu, M.T.H.; Bonneau, R. Laser flash photolysis study of substituent effects on the rate of 1,2-H migration in a series of benzylchlorocarbenes. J. Am. Chem. Soc., 1992, 114, 3604-3607.
101. Evanseck, J.D.; Houk, K.N. Theoretical predictions of activation energies for 1,2-hydrogen shifts in singlet carbenes. J. Phys. Chem., 1990, 94, 5518-5523.
102. Reed, S.C.; Modarelli, D.A. Conformational effects on the excited state 1,2-hydrogen migration in alkyldiazomethanes. Tetrahedron Lett., 1996, 37, 7209-7212.
103. Moriconi, E.J.; Murray, J.J. Pyrolysis + Photolysis of 1-Methyl-3-Diazooxindole. Base decomposition of isatin 2-Tosylhydrazone. J. Org. Chem., 1964, 29, 3577-3584.
104. Miller, D.J.; Moody, C.J. Synthetic applications of the O-H Insertion reactions of carbenes and carbenoids derived from diazocarbonyl and related diazo-compounds. Tetrahedron, 1995, 51, 10811-10843.
105. Kirmse, W.; Kilian, J.; Steenken, S. Carbenes and the oxygen-hydrogen bond: spectroscopic evidence for protonation of diarylcarbenes to give diarylcarbenium ions. J. Am. Chem. Soc., 1990, 112, 6399-6400.
106. Belt, S.T.; Bohne, C.; Charette, G.; Sugamori, S.E.; Scaiano, J.C. Carbocation formation via carbene protonation studied by the technique of stopped-flow laser-flash photolysis. J. Am. Chem. Soc., 1993, 115, 2200-2205.
107. Peon, J.; Polshakov, D.; Kohler, B. Solvent reorganization controls the rate of proton transfer from neat alcohol solvents to singlet diphenylcarbene. J. Am. Chem. Soc., 2002, 124, 6428-6438.
108. Wang, J.; Kubicki, J.; Gustafson, T.L.; Platz, M.S. The dynamics of carbene solvation: an ultrafast study of p-Biphenylyltrifluoromethylcarbene. J. Am. Chem. Soc., 2008, 130, 2304-2313.
109. Chiang, Y.; Kresge, A.J.; Popik, V.V.; Schepp, N.P. The mandelic acid keto-enol system in aqueous solution, generation of the enol by hydration of phenylhydroxyketene and phenylcarboxycarbene. J. Am. Chem. Soc., 1997, 119, 10203-10212.
110. Chiang, Y.; Jefferson, E.A.; Kresge, A.J.; Popik, V.V.; Xie, R.Q. Conjugate addition of water to a-carbonylcarbenes. J. Phys. Org. Chem., 1998, 11, 610-613.
111. Schepp, N.P.; Wirz, J. Effect of a-Carbomethoxy group on the reactivity of benzyl cations in solution. J. Am. Chem. Soc., 1994, 116, 11749-11753.
112. Tomioka, H.; Inagaki, T.; Izawa, Y. Photolysis of a-diazobenzyl-phosphonates in alcoholic matrices at 77K. J. Chem. Soc. Chem. Commun., 1976, 24, 1023-1024.
113. Tomioka, H.; Inagaki, T.; Nakamura, S.; Izawa, Y. Temperature-dependence of product distributions in the photolysis of a-Diazobenzylphosphonates in alcohols. J. Chem. Soc. Perkin Trans. 1, 1979, 1, 130-134.
114. Tomioka, H.; Hirai, K. Neighboring phosphonate group participation in carbene chemistry. J. Chem. Soc. Chem. Commun., 1990, 22, 1611-1612.
115. Rando, R.R. Conformational and solvent effects on carbene reactions. J. Am. Chem. Soc., 1970, 92, 6706-6707.
116. Wydila, J.; Thornton, E.R. Photolysis studies of a-Diazoamides the effect of carboxamide substituents on selectivity ratios. Tetrahedron Lett., 1983, 24, 233-236.
117. Meerwein, H.; Rathjen, H.; Werner, H. Die methylierung von RH-verbindungen mittels diazomethans unter mitwirkung des lichtes. Ber. Dtsch. Chem. Ges., 1942, 75, 1610-1622.
118. Doering, W.V.E.; Knox, L.H.; Jones, M. Reaction of methylene with diethyl ether and tetrahydrofuran. J. Org. Chem., 1959, 24, 136-137.
119. Tomioka, H.; Itoh, M.; Yamakawa, S.; Izawa, Y. The reactivity of carbenes from photolysis of diazo-compounds towards carbon-hydrogen bonds - effects of structure, temperature, and matrix on the insertion selectivity. J. Chem. Soc. Perkin Trans. 2, 1980, 4, 603-609.
120. Jones, M.; Ando, W.; Hendrick, M.E.; Kulczycki, A.; Howley, P.M.; Hummel, K.F.; Malament, D.S. Irradiation of methyl diazomalonate in solution. Reactions of singlet and triplet carbenes with carbon-carbon double bonds. J. Am. Chem. Soc., 1972, 94, 7469-7479.
121. Sander, W.; Strehl, A.; Winkler, M. Photochemistry of bis(sulfonyl)diazomethanes. Eur. J. Org. Chem., 2001, 20, 3771-3778.
122. Moss, R.A.; Dolling, U.H. Photolysis of phenyldiazomethane in olefinic matrices - chemistry of triplet phenylcarbene. J. Am. Chem. Soc., 1971, 93, 954-960.
123. Tomioka, H.; Ozaki, Y.; Izawa, Y. Mechanism of C-H insertion of carbene in rigid matrix. Chem. Lett., 1982, 6, 843-846.
124. Barcus, R.L.; Hadel, L.M.; Johnston, L.J.; Platz, M.S.; Savino, T.G.; Scaiano, J.C. 1-Naphthylcarbene: spectroscopy, kinetics, and mechanisms. J. Am. Chem. Soc., 1986, 108, 3928-3937.
125. Corey, E.J.; Felix, A.M. A new synthetic approach to penicillins. J. Am. Chem. Soc., 1965, 87, 2518-2519.
126. Lowe, G.; Parker, J. Photochemical conversion of a-diazo-amides and a-diazo-esters into b-Lactams and b-Lactones and g-Lactones. J. Chem. Soc. D Chem. Commun., 1971, 11, 577-578.
127. Kirmse, W.; Dietrich, H. Zerfallsreaktionen des diazoessigsäureallylesters. Chem. Ber., 1965, 98, 4027-4032.
128. Kirmse, W.; Dietrich, H.; Bucking, H.W. Intramolekulare reaktionen von alkoxycarbonylcarbenen. Tetrahedron Lett., 1967, 19, 1833-1835.
129. Rando, R.R. Conformational and medium effects on intramolecular carbene reactions. J. Am. Chem. Soc., 1972, 94, 1629-1631.
130. Tomioka, H.; Kitagawa, H.; Izawa, Y. Photolysis of N,N-Diethyldiazoacetamide - Participation of a non-carbenic process in intra-molecular carbon-hydrogen insertion. J. Org. Chem., 1979, 44, 3072-3075.
131. Tomioka, H.; Kondo, M.; Izawa, Y. Substituent effects on the product distribution in diazo amide photochemistry. Role of ground-state conformational populations. J. Org. Chem., 1981, 46, 1090-1094.
132. Kaplan, F.; Meloy, G.K. Structure of Diazoketones. A Study of hindered internal rotation. J. Am. Chem. Soc., 1966, 88, 950-956.
133. Candeias, N. R.; Gois, P. M. P.; Veiros, L. F.; Afonso, C. A. M. C-H carbene insertion of a-Diazo acetamides by Photolysis in nonconventional media. J. Org. Chem., 2008, 73, 5926-5932.
134. Maas, G.; Krebs, F.; Werle, T.; Gettwert, V.; Striegler, R. Silicon-oxygen heterocycles from thermal, photochemical, and transitionmetal catalyzed decomposition of a-(alkoxysilyl and alkenyloxysilyl)-a-diazoacetates. Eur. J. Org. Chem., 1999, 8, 1939-1946.
135. DoMinh, T.; Strausz, O.P.; Gunning, H.E. Photochemistry of diazo esters .2. a Novel Reaction Path. J. Am. Chem. Soc., 1969, 91, 1261-1263.
136. von E. Doering, W.; Hoffmann, A.K. The addition of dichlorocarbene to olefins. J. Am. Chem. Soc., 1954, 76, 6162-6165.
137. Skell, P.S.; Garner, A.Y. The stereochemistry of carbene-olefin reactions. Reactions of dibromocarbene with the cis- and trans-2-Butenes. J. Am. Chem. Soc., 1956, 78, 3409-3411.
138. Doering, von E.W.; LaFlamme, P. The cis addition of dibromocarbene and methylene to cis- and trans-butene. J. Am. Chem. Soc., 1956, 78, 5447-5448.
139. 2. J. Am. Chem. Soc., 1956, 78, 4496-4497.
140. Roth, H.D. Chemically induced nuclear spin polarization in the study of carbene reaction mechanisms. Acc. Chem. Res., 1977, 10, 85-91.
141. Moss, R.A. Carbenic selectivity in cyclopropanation reactions. Acc. Chem. Res., 1980, 13, 58-64.
142. Moss, R.A.; Joyce, M.A. Reactions of methylphenylcarbene and phenylcarbene in isobutene matrices: origins of the "insertion" products. J. Am. Chem. Soc., 1977, 99, 1262-1264.
143. Moss, R.A.; Joyce, M.A. Chemistry of fluorenylidene at low temperatures. J. Am. Chem. Soc., 1978, 100, 4475-4480.
144. Tomioka, H.; Komatsu, K.; Shimizu, M. Photochemistry of matrix-isolated (a-diazobenzyl)phosphonate. Observation and reactions of phosphonylphenylcarbene, phosphonyl phenyl ketone oxide, and phenylphosphonyldioxirane. J. Org. Chem., 1992, 57, 6216-6222.
145. Arnold, B.R.; Scaiano, J.C.; Bucher, G.F.; Sander, W.W. Laser flash photolysis studies on 4-oxocyclohexa-2,5-dienylidenes. J. Org. Chem., 1992, 57, 6469-6474.
146. Nojima, T.; Ishiguro, K.; Sawaki, Y. Mechanistic study on the reaction of phenyldiazomethanes with singlet oxygen: formation and cycloreversion of 1,2,3,4-Dioxadiazole intermediates. J. Org. Chem., 1997, 62, 6911-6917.
147. Nojima, T.; Hirano, Y.; Ishiguro, K.; Sawaki, Y. Dramatic change of carbonyl oxide reactivity by the potent electron-withdrawing trifluoromethyl group. J. Org. Chem., 1997, 62, 2387-2395.