SYNTHESIS OF ALKYLIDENECYCLOPROPANES VIA THERMAL CYCLOREVERSION OF ALPHA-SPIROCYCLOPROPYL-BETA-LACTONES

Authors
DANHEISER RL LEE TW MENICHINCHERI M BRUNELLI S NISHIUCHI M
Citation
Rl. Danheiser et al., SYNTHESIS OF ALKYLIDENECYCLOPROPANES VIA THERMAL CYCLOREVERSION OF ALPHA-SPIROCYCLOPROPYL-BETA-LACTONES, Synlett, (5), 1997, pp. 469
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
5
Year of publication
1997
Database
ISI
SICI code
0936-5214(1997):5<469:SOAVTC>2.0.ZU;2-1
Abstract
An efficient two-step synthesis of alkylidenecyclopropanes is reported based on the addition of metallated cyclopropyl thiol esters to carbo nyl compounds. Thermolysis of the resulting alpha-spiro-cyclopropyl-be ta-lactones at 105-150 degrees C induces thermal [2+2] cycloreversion to furnish alkylidenecyclopropanes in good yield.