ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19930760134
Permalink
