Photo-Ritter Reaction of Arylmethyl Bromides in Acetonitrile

REFERENCES

• (a) Ritter , J. J. ; Minieri , P. P. A New reaction of nitriles, I: Amides from alkenes and mononitriles . J. Am. Chem. Soc. 1948 , 70 , 4045 – 4048 ; (b) Ritter , J. J. ; Kalish , J. A new reaction of nitriles, II: Synthesis of t-carbinamines . J. Am. Chem. Soc. 1948 , 70 , 4048 – 4050 ; (c) Krimen , L. I. ; Cota , D. J. Org. React., Vol. 17: The Ritter Reaction; John Wiley & Sons: New York, 1969, pp. 213–325.
   PubMed Web of Science ®Google Scholar
• Bishop , R. Comp. Org. Synth.: Ritter-type Reaction ; B. M. Trost and I. Fleming (Eds.) ; Pergamon Press : New York , 1991 .
   Google Scholar
• Two recent examples: (a) Yadav , J. S. ; Reddy , B. V. S. ; Pandurangam , T. ; Reddy , Y. J. PMA/SiO2-catalyzed amidation of alcohols with nitriles: A simple, cost-effective, and recyclable catalytic system for Ritter reaction . Catal. Commun. 2008 , 9 , 1297 – 1301 ; (b) Barbero , M. ; Bazzi , S. ; Cadamuro , S. ; Dughera , S. o-Benzenedisulfonimide as a reusable Brønsted acid catalyst for Ritter-type reactions . Eur. J. Org. Chem. 2009 , 430 – 436 .
   Web of Science ®Google Scholar
• (a) Mattes , S. L. ; Farid , S. Photosensitized electron-transfer reactions of phenylacetylene . J. Chem. Soc., Chem. Commun. 1980 , 126 – 129 ; (b) Zona , T. A. ; Goodman , J. L. Stereospecific cycloreversion of an azoalkane cation radical: The role of the 1,4-biradical . J. Am. Chem. Soc. 1993 , 115 , 4925 – 4926 ; (c) de Lijser , H. J. P. ; Arnold , D. R. Radical ions in photochemistry, 44: The photo-NOCAS reaction with acetonitrile as the nucleophile . J. Org. Chem. 1997 , 62 , 8432 – 8438 ; (d) Ishii , H. ; Hirano , T. ; Maki , S. ; Niwa , H. ; Ohashit , M. A novel, stereoselective photo-Ritter reaction of 1,1-diphenyl-l,6-heptadiene via photoinduced electron transfer reaction . Tetrahedron Lett. 1998 , 39 , 2791 – 2792 .
   Google Scholar
• Kropp , P. J. ; Poindexter , G. S. ; Pienta , N. J. ; Hamilton , D. C. Photochemistry of alkyl halides, 4: 1-Norbornul, 1-norbornylmethyl, 1- and 2-adamantyl, and 1-octyl bromides and iodies . J. Am. Chem. Soc. 1976 , 98 , 8135 – 8144 .
   Google Scholar
• Kitamura , T. ; Kobayashi , S. ; Taniguchi , H. Isoquinoline derivatives from the Ritter-type reaction of vinyl cation . Chem. Lett. 1984 , 1351 – 1352 .
   Google Scholar
• Guizzardi , B. ; Mella , M. ; Fagnoni , M. ; Albini , A. Photochemical reaction of N,N-dimethyl-4-chloroaniline with dienes: New synthetic paths via a phenyl cation . Chem. Eur. J. 2003 , 9 , 1549 – 1555 .
   PubMedGoogle Scholar
• Košmrlj , B. ; Šket , B. Photolysis of bromo- and chloro-substituted benzyl derivatives: Competition between ionic and radical pathways. J. Org. Chem. 2000, 65, 6890–6896.
   PubMedGoogle Scholar
• (a) Neunteufel , R. A. ; Arnold , D. R. Radical ions in photochemistry, I: 1,1-Diphenylethylene cation radical . J. Am. Chem. Soc. 1973 , 95 , 4080 – 4081 ; (b) Majima , T. ; Pac , C. ; Nakasone , A. ; Sakurai , H. Redox-photosensitized reactions, 7: Aromatic hydrocarbon-photosensitized electron-transfer reactions of furan, methylated furans, 1,1-diphenylethylene, and indene with p-dicyanobenzene . J. Am. Chem. Soc. 1981 , 103 , 4499 – 4508 ; (c) Mattes , S. L. ; Farid , S. Photochemical electron-transfer reactions of 1,1-diarylethylenes . J. Am. Chem. Soc. 1986 , 108 , 7356 – 7361 ; (d) Hoffmann , U. ; Gao , Y. ; Pandey , B. ; Klinge , S. ; Warzecha , K.-D. ; Krtiger , C. ; Roth , H. D. ; Demuth , M. Light-induced polyene cyclizations via radical cations in micellar medium . J. Am. Chem. Soc. 1993 , 115 , 10358 – 10359 ; (e) Heinemann , C. ; Demuth , M. Biomimetic cascade cyclizations of terpenoid polyalkenes via photoinduced electron transfer: Long-distance asymmetric induction by a chiral auxiliary . J. Am. Chem. Soc. 1997 , 119 , 1129 – 1130 .
   Google Scholar
• Murov , S. L. ; Carmichael , I. ; Hug , G. L. Handbook of Photochemistry, ed , 2nd .; Marcel Dekker Inc. : New York , 1993 .
   Google Scholar
• (a) Nicholas , H. O. ; Erickson , J. L. E. Substituted amides, I: The preparation of substituted acetamides and the corresponding primary amines . J. Am. Chem. Soc. 1926 , 48 , 2174 – 2176 ; (b) Parris , C. L. ; Christenson , R. M. N-Alkylation of nitriles with benzyl alcohol, related alcohols, and glycols . J. Org. Chem. 1960 , 25 , 331 – 334 , and references cited therein ; (c) Freudenreich , C. ; Samama , J.-P. ; Biellmann , J.-F. Design of inhibitors from the three-dimensional structure of alcohol dehydrogenase: Chemical synthesis and enzymatic properties . J. Am. Chem. Soc. 1984 , 106 , 3344 – 3353 ; (d) Darbeau , R. W. ; White , E. H. ; Song , F. H. ; Darbeau , N. R. ; Chou , J. A study of essentially free carbocations derived via diazonium and oxo diazonium ions in the liquid phase . J. Org. Chem. 1999 , 64 , 5966 – 5978 ; (e) Wille , U. ; Heuger , G. ; Jargstorff , C. N-Centered radicals in self-terminating radical cyclizations: Experimental and computational studies . J. Org. Chem. 2008 , 73 , 1413 – 1421 .
   Google Scholar
• (a) Imrie , C. ; Modro , T. A. ; Rohwer , E. R. ; Wagener , C. C. P. Photolysis of (arylmethyl) triphenylphosphonium salts: Substituent, counterion, and solvent effects on reaction products . J. Org. Chem. 1993 , 58 , 5643 – 5649 ; (b) Yavari , I. ; Sabbaghan , M. Synthesis of functionalized pyrroles by reaction of 3,4-diacetylhexane-2,5-dione with primary amines in water . Synth. Commun. 2007 , 37 , 1791 – 1800 .
   Google Scholar