Issue 0, 1980
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

SN′ reactions on some cyclopentene derivatives employing simple nucleophiles and organocuprate reagents

Christopher B. Chapleo,   Mark A. W. Finch,   Stanley M. Roberts,   Geoffrey T. Woolley,   Roger F. Newton  and  David W. Selby  

Abstract

The cyclopentenyl bromides (1) and (9) react with thiophenoxide ion in SN′syn-fashion with very high selectivity. The bromide (4) reacts with the same nucleophile to give the products of SN2 and SN2′syn-reactions. The lactones (1), (4), (15), and (16) react with lithium dibutylcuprate in the SN′ anti-fashion predominantly, while the esters (9) and (11) react via the SN′syn-mode preferentially. Mechanisms are presented to explain the substitution patterns observed for the cuprate reactions.

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Article information

DOI
https://doi.org/10.1039/P19800001847
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1980, 1847-1852

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S N ′ reactions on some cyclopentene derivatives employing simple nucleophiles and organocuprate reagents

C. B. Chapleo, M. A. W. Finch, S. M. Roberts, G. T. Woolley, R. F. Newton and D. W. Selby, J. Chem. Soc., Perkin Trans. 1, 1980, 1847 DOI: 10.1039/P19800001847

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