Neighboring Group participation by the tetrahydrofuran ring
作者:
George T. Kwiatkowski,
Spiro J. Kavarnos,
W. D. Closson,
期刊:
Journal of Heterocyclic Chemistry
(WILEY Available online 1965)
卷期:
Volume 2,
issue 1
页码: 11-14
ISSN:0022-152X
年代: 1965
DOI:10.1002/jhet.5570020103
出版商: Wiley‐Blackwell
数据来源: WILEY
摘要:
AbstractNeighboring group participation in the solvolytic reactions of a series of ω‐(2‐tetx‐a‐hydrofuran)alkylp‐ bromobenzenesulfonate esters has been investigated. Anchimeric assistance to solvolysis is most pronounced in the case of 3‐(2‐tetrahydrofuran)propylp‐bromobenzenesulfonate where a 1‐oxabicyclo[3.3.0]octane cation can form. A “special salt effect” and an “induced common ion effect” were observed in the acetolysis of this ester. It appears that the tetrahydrofuran ring is about twice as effective as the methoxyl group in neigh
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