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Reaction of cyclopropylcarbene-chromium complexes with alkenes; Synthesis of cyclopropylcyclopropanes

✍ Scribed by James W. Herndon; Seniz U. Tumer

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
258 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

We have examined the reaction of cyclopropylcarbene-chromium complexes with alkenes. The reaction leads to the formation of cyclopropylcyclopropane derivatives in good yield, accompanied by minor amounts of ring-opened products.

Conjugated dienes and a&unsaturated esters and amides appear to be suitable substrates for the reaction.

Recently, cyclopropylcarbene-chromium complexes have emerged as valuable reagents for organic synthesis, coupling with alkynes to give cyclopentenones (2) in good-excellent yields' (Scheme 1). During this transformation, a net ring opening of the original cyclopropane ring occurs and ethylene is expelled.

We recently reported thermolysis studies of cyclopropylcarbene-chromium complexes2.

In these studies, we showed that the cyclopropane ring in these complexes is very reluctant to undergo ring-opening processes unless the ring is activated by the presence of alkenyl substituents. Since

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