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Scientific article
English

Structural Effects on the RhII-Catalyzed Rearrangement of Cyclopropenes

Published inHelvetica Chimica Acta, vol. 76, no. 1, p. 521-534
Publication date1993
Abstract

The thermocatalytic rearrangement of 2-alkylcycloprop-2-ene-1-carboxylates (1) in the presence of RhII perfluorobutyrate is regio- and stereospecific and leads to the substituted metallocarbenes 3. The latter undergo intramolecular C-H bond insertion to form cyclopentylidenes (4). In contrast, the metallocarbenes 19, derived from 2,3-dialkylcycloprop-2-ene-1-carboxylates 6c, d, react to dienes (Z)-20, via 1,2-H migration. The cyclopropenedicarboxylates 10, in turn, rearrange exclusively to the more substituted metallocarbenes 26, which cyclize to furans 28, With 6e, and 12, products derived from both modes of ring-opening are observed.

Funding
  • Swiss National Science Foundation - 20-32117.91
Citation (ISO format)
MULLER, Paul, GRAENICHER, Christian. Structural Effects on the Rh<sup>II</sup>-Catalyzed Rearrangement of Cyclopropenes. In: Helvetica Chimica Acta, 1993, vol. 76, n° 1, p. 521–534. doi: 10.1002/hlca.19930760134
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Article (Published version)
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ISSN of the journal0018-019X
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