An unusual fragmentation of oxetane-embedded tetracyclic ketal systems

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.

[error in script]

IITH Creators:	IITH Creators ORCiD Khan, Faiz Ahmed UNSPECIFIED
Item Type:	Article
Uncontrolled Keywords:	Cyclobutanes; Fragmentation reactions; Functionalized; High yield; Norbornane; Side products
Subjects:	Chemistry
Divisions:	Department of Chemistry
Depositing User:	Team Library
Date Deposited:	15 Nov 2014 09:08
Last Modified:	21 Sep 2017 06:44
URI:	http://raiithold.iith.ac.in/id/eprint/804
Publisher URL:	https://doi.org/10.1021/jo401870s
OA policy:	http://www.sherpa.ac.uk/romeo/issn/0022-3263/
Related URLs:	Google Scholar

Actions (login required)

View Item

Statistics for this ePrint Item