The predictable behaviour of cations deriving from endo-4-chlorotetracyclo[3.3.0.0.{2,8}O.{3,6}]octane

Jefford, Charles; Genevay-Höck, Suzanne; Delay, Arlette; Mareda, Jiri; Burger, Ulrich

doi:10.1016/S0040-4039(01)86345-0

Scientific article

Letter

English

The predictable behaviour of cations deriving from endo-4-chlorotetracyclo[3.3.0.0.{2,8}O.{3,6}]octane

ContributorsJefford, Charles; Genevay-Höck, Suzanne; Delay, Arlette; Mareda, Jiri; Burger, Ulrich

Published inTetrahedron letters, vol. 20, no. 27, p. 2549-2552

Publication date1979

Abstract

Silver cation-initiated ionization of the title compound in aqueous dioxane gives the exo and endo-tetracyclo[3.3.0.0.2,8O.4,6]octane-3-ols (35 and 65%). Thermal isomerization in chloroform gives the exo and endo isomers of 4-chlorobicyclo[3.2.1]octa-2,6-dienes (3.5 and 1.5%) and 6-chlorotricyclo[3.2.1.0.2,7]oct-3-ene (90 and 5%). The behaviour of the cations involved is compatible with MINDO/3 calculations.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

JEFFORD, Charles et al. The predictable behaviour of cations deriving from endo-4-chlorotetracyclo[3.3.0.0.{2,8}O.{3,6}]octane. In: Tetrahedron letters, 1979, vol. 20, n° 27, p. 2549–2552. doi: 10.1016/S0040-4039(01)86345-0

Identifiers

PID : unige:6235
DOI : 10.1016/S0040-4039(01)86345-0

Journal ISSN0040-4039

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The predictable behaviour of cations deriving from endo-4-chlorotetracyclo[3.3.0.0.{2,8}O.{3,6}]octane

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