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Conclusive evidence for [3,3] sigmatropic rearrangement in the solvolysis of some bridged tricyclic tosylates

✍ Scribed by Yutaka Fujise; Tetsuo Nakatsu; Akira Nakamura; Shô Itô

Book ID: 104246229
Publisher: Elsevier Science
Year: 1978
Tongue: French
Weight: 256 KB
Volume: 19
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)95205-0

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✦ Synopsis

In the previous paper ') we have reported the solvolysis of z-tricycloE4.4.1. 12r51dodeca-3,7-dienanti-l 1 yl and -3,7,9-trien-anti-11 -yl tosylates (I=OTs and z-OTs), --In the former reaction, the products derived from the ion j3_ were isolated. Since cycloheptatriene and cyclopentadiene do not undergo cycloaddition reaction under the same conditions, the fact is only rationalized by the C3,3 sigmatropy of the ion J. This rearrangement is unique in that the two three-carbon moieties, C3C4C5 and CsC7C8, have to inter-10) J. A. Berson and J. M. Janusz, J. Amer. Chem. Sot., Prof. Berson (Apr. 10, 1978). 2, 5939 (1974) and private communication from 11) U.

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