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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. 259 Optimum conditions have been found for [4 + 31 cycloadditions of simple allyl carbonium ions and conjugated dienes, they involve stirring the diene with the allyl iodide and silver trifluoroacetate in isopentane a t -78”.
J. Miller, Austral. J. , 24, 2013 (1971). 166 187 Carbonium Ions 31 OTs OTs (119) (121) OTS OTs (125) * &OPNB Organic Reaction Mechanisms 197I 32 119P\ Reactions of Cyclopropyl Derivatives Heating the dichlorocyclopropane derivative (132) a t 160" for 4 hr gave a mixture of (133) and (134) in the ratio 91 : 9 ; similarly, (135) gave the same allyl chlorides in the ratio 14:86. The rearrangement was shown to be largely stereospecifio since, when heated with sodium methoxide in methanol, both (132) and (133) gave the methyl ethers (136)and (137)in the same ratio 87 : 13.
252 J. W. Larsen, P. A. Bouis, M. W. Grant, and C. 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).