Issue 88, 2015
From the journal:

RSC Advances

Synthesis of 1,5-dioxocanes via the two-fold C–O bond forming nucleophilic 4 + 4-cyclodimerization of cycloprop-2-en-1-ylmethanols†

Andrew Edwards,a   Trevor Bennin,ab   Marina Rubinaa  and  Michael Rubin*ac  

* Corresponding authors

a Department of Chemistry, University of Kansas, 1251, Wescoe Hall Dr., Lawrence, KS 66045-7582, USA
E-mail: mrubin@ku.edu

b Department of Chemistry, Northland College, 1411 Ellis Avenue, Ashland, Wisconsin 54806-3999, USA

c Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355009, Russia

Abstract

An efficient [4 + 4] cyclodimerization of cyclopropenemethanols operating via a two-fold strain release-driven addition of alkoxides across the double bond of cyclopropenes was investigated. This chemo- and diastereoselective transformation provided previously unknown 2,7-dioxatricyclo[7.1.0.04,6]decane scaffolds.

Graphical abstract: Synthesis of 1,5-dioxocanes via the two-fold C–O bond forming nucleophilic 4 + 4-cyclodimerization of cycloprop-2-en-1-ylmethanols

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Article information

DOI
https://doi.org/10.1039/C5RA14077C
Article type
Communication
Submitted
16 Jul 2015
Accepted
18 Aug 2015
First published
19 Aug 2015

RSC Adv., 2015,5, 71849-71853

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Synthesis of 1,5-dioxocanes via the two-fold C–O bond forming nucleophilic 4 + 4-cyclodimerization of cycloprop-2-en-1-ylmethanols

A. Edwards, T. Bennin, M. Rubina and M. Rubin, RSC Adv., 2015, 5, 71849 DOI: 10.1039/C5RA14077C

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