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Ring opening reactions of deltacyclene epoxides

✍ Scribed by Mark Lautens; Catherine M. Crudden

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 249 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)80512-8

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✦ Synopsis

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A series of epoxides from reaction of substituted deltacyclenes with metu-chloroperbenzoic acid are reported. These compounds were found to react with BFs.Et20 in MeOH/&O to yield ring-opened products.

Rearrangements were noted in some cases depending on the substitution pattern.

We have been interested in determining the utility of the homo-Diels Alder cycloaddition as a means of preparing natural and unnatural products. 2.3 This reaction is represented by the coupling of a substituted acetylene with norbornadiene(NBD) to yield a deltacyclene (eq. 1). We have recently shown that an activated cobalt complex

& / /

Co(acac)a, 4 eq. &AU

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