Organic Reaction Mechanisms 1968


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Beak and R. J. Trancik, J . Am. ,90,2714 (1988). 54 H. W. Whitlock and M. W. Siefken, J . Am. , 90,4929 (1968). 55 B. R. Vogt, S. R. Suter and J. R. E. R. 50 51 Vogt, ibid. p. 1676. 68The rate is 3040 times that for ethyl toluene-p-sulphonate and taking into account the expected deactivating inductive effect of the phenyl ring, this indicates that the transition state is stabilized by about 7 kcal mole-l through phenyl participation. The ionic intermediate is therefore stabilized by about 14 kcal mole-l, on the assumption that it stabilized by double the amount that the transition state is.

ISBS, 1129. 73 74 30 Organic Reaction Machanisms 1968 butyl hydroperoxide decomposes very rapidly to ring-expanded products7‘ (see also p. 269). '^ Participationby Double and Triple Bonds7s The relative rates of solvolysis of 7-p-anisylnorbornen-unti-7-yl p-nitrobenzoate (73) in 9O:lO (CH8),CO-H20 or 30:70 THF-MeOH indicate that there is no participation by the double bond. The products from these reactions were identical to those from the syn-isomer (74) and consisted of 94 f1% anti- and 6 f 1% syn-alcohol or ether.

Chem. , 90, 4196 (1968). 40 Organic Beaction Mechanisms 1968 H H I R estimated on the basis of the carbonyl stretching frequency of the corresponding ketone that the rate of acetolysis of (110) is considerably enhanced. The cyclopropyl ring therefore dbilizes the transition state but the ionic intermediate always reverts to cyclopropylmethyl rather than to homoallylic products. log The rates and products of the hydrolyses of the spirocyclopropylmethyl dinitrobenzoates (112)-(114) in aqueous acetone at 100" are SB shown.

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