The Journal of Organic Chemistry

The ester enolate Carroll rearrangement

SR Wilson, MF Price

Index: Wilson , Stephen R.; Price, Martyn F. Journal of Organic Chemistry, 1984 , vol. 49, # 4 p. 722 - 725

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Citation Number: 67

Abstract

6 H a CH, CH, CH, CH= C (CH,),. with theoretical calculations of Carpenter, ls where electron-withdrawing substituents at the 1-position increase the energy of activation for rearrangement. Whereas pyrolysis occasionally gives allylic regioisomers (cf. entries 1, 2, and 6, Table I) formally representing [3, 3] and [1, 3] rearrangements," the rearrangement of the dianions gives exclusively the expected [3, 3] products. Evidence18 suggests that the ...