Journal of the Chemical Society. Perkin transactions I p. 1847 - 1852 (1980)
Update date:2022-08-04
Topics:
Chapleo, Christopher B.
Finch, Mark A. W.
Roberts, Stanley M.
Woolley, Geoffrey T.
Newton, Roger F.
Selby, David W.
The cyclopentenyl bromides (1) and (9) react with thiophenoxide ion in SN' syn-fasion 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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