Organic Reaction Mechanisms 1971 by B.; Rees, C.W. (editors) Capon

By B.; Rees, C.W. (editors) Capon


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196 W. E. Dupuy, H. R. Hudson, and P. A. Karam, Tetrahedron Letters, 1971, 3193. 197 C. C. Lee and J. Law, Can. J . , 49,2746 (1971). 198 M. A. MeKinney, S. H. Smith, S. Hempelman, M. M. Gearen, B. U. M. Pearson, and L. Pearson, Tetrahedron Letters, 1971, 3657. 199 J. A. Peters and H. van Bekkum, Rec. Truv. , 9 0 , 6 5 (1971). 200 J. B. Hendriekson and R. K. , J . Am. Chem. , 93,4491 (1971). 201 T. S. Sorensen and C. R. Jablonski, J . Organomet. , 25, C62 (1970); C. P. Lillya and R. A. Sahatjian, J .

Porter, and D. P. Kelly, J . Am. Chem. ,93, 464 (1971). 28s G. A. Olah and Y. K. Mo, J . Am. Chem. ,93,4942 (1971). 229 42 Organic Reaction Mechanisms 1971 the three-centre-bond transition state was found in the formation of the t-butyl carbonium ion, rather than isobutene, on treatment of isobutane with DS03F-SbF5 or DF-SbF5 at -78" and also by hydrogen-deuterium exchange of adamantane in DF-SbF5. Isobutane yielded methane and isopropyl cation and C-C bond protolysis in n-alkanes was shown to be a general reaction.

A. Lane, J. Am. Chem. , 253 J. Larsen and S. Ewing, J . Am. Chem. ,93, 5107 (1971). 254 M. L. Sinnott and M. C. Whiting, J . Chem. (B), 1971, 965. W. 255 256 93,2067 (1971). R. K. Crossland, W. E. Wells, and V. J. , J . Am. Chem. ,93,4217 (1971). M. D. Bentley and J. A. Lacadie, Tetrahedron Letters, 1971, 741. 44 Organic Reaction Mechanisms 1971 The extent of fragmentation in the reaction of the series of tertiary alcohols (177) increases with the size of R (Table 1). 2-Me HMC(Mez’But R Me /l-Bu RCH2\+ ,C-C’%,,,Me Me L Me \&$ 4% bMe shift CHzR (177) c- f -Bu Me E CH2 R RCHz - t-Bu+ HE Me Me (179) (178) Table 1.

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