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The Addition of 2-Oxido-2-cyclopenten-1-ylium to Some Olefins and Dienes in 2,2,2-Trifluoroethanol

✍ Scribed by Johannes Leitich; Ingeborg Heise

Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 448 KB
Volume: 2001
Category: Article
ISSN: 1434-193X
DOI: 10.1002/1099-0690(200107)2001:14<2707::aid-ejoc2707>3.0.co;2-c

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✦ Synopsis

The title reaction has been studied with 2-methoxypropene, (E)-cyclooctene, ethoxyethene, 1,3-cyclopentadiene, 3methylenecyclohexene, styrene and isoprene as the olefinic substrates. This sequence is one of decreasing reactivity of the substrates towards 2-oxido-2-cyclopenten-1-ylium (1) if [4 + 3] cycloaddition (the prevailing reaction in the case of cyclopentadiene and isoprene) is ignored. This reactivity encompasses: (a) the formation of intermediate 1,5-dipoles, which in the majority of cases give rise to a multitude of products including many of higher molecular mass, and (b) two types of ene reactions, dubbed ''ene-type 1'' and ''ene-type 2''. Type 1, in which the migrating hydrogen atom is abstracted from 1, is ubiquitous (except with 2-methoxypropene) but is always a minor reaction; type 2, in which the migrating Scheme 1

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