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The Thermal Reaction of Substituted Vinylcyclopropanes with Iron Pentacarbonyl
Author(s) -
Sarel S.,
BenShoshan R.,
Kirson B.
Publication year - 1972
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.197200079
Subject(s) - chemistry , cyclopropane , ring (chemistry) , aryl , photochemistry , medicinal chemistry , organic chemistry , alkyl
The thermal reactions of 1‐aryl‐1‐cyclopropylethylenes and 1,1‐dicyclopropylethylene with pentacarbonyliron are investigated. Reactions of the former substrates yield 2‐aryl‐1,3‐pentadiene‐tricarbonyliron complexes via cyclopropane ring opening, hydrogen migration and coordination to iron. Reaction with the latter substrate gives 2‐cyclopropyl‐1,3‐pentadienetricarbonyliron in similar fashion, and, in addition, 3‐(1′‐propenyl)‐cyclohex‐2‐enone tricarbonyliron derived from the opening of the second ring coupled with carbon monoxide insertion. The cyclopropane ring serves as a two π‐electron donor in these reactions, and the vinylcyclopropane system emerges as a novel source of four π‐electrons which are available to coordination in direct analogy to reactions of formal diene systems with iron carbonyls.