Mangeswara Rao, G H and Khan, Faiz Ahmed
(2013)
An unusual fragmentation of oxetane-embedded tetracyclic ketal systems.
Journal of Organic Chemistry, 78 (21).
pp. 11092-11095.
ISSN 0022-3263
Full text not available from this repository.
(
Request a copy)
Abstract
An unusual route for the synthesis of functionalized cyclobutane derivatives starting from functionalized norbornane derivatives is reported. Base-induced fragmentation of an oxetanol-type moiety embedded in a tetracyclic norbornyl ketal leads to a cyclobutane-fused derivative as the major or exclusive product. The fragmentation reaction for bridgehead-bromine-substituted derivatives was much faster than for the corresponding chlorine-substituted substrates. The functionalized cyclobutane product was formed exclusively in high yield in the former case, while the latter furnished a minor uncyclized side product in varying yields.
Actions (login required)
|
View Item |