ChemInform Abstract: Methoxycarbonyl Migration in 3-Methylene-1,4-cyclohexadienes. An Extension of the von Auwers Rearrangement
- Resource Type
- Authors
- Raphael F. Guignard; Mehdi Boumediene; Samir Z. Zard
- Source
- ChemInform. 47
- Subject
- chemistry.chemical_compound
chemistry
Cyclohexadienes
Aromatization
Substituent
General Medicine
Methylene
Medicinal chemistry
- Language
- ISSN
- 0931-7597
Upon heating, 3-methylene-1,4-cyclohexadienes possessing an alkoxycarbonyl substituent in position 6 undergo rearrangement and concomitant aromatization to give the corresponding arylacetates. This transformation represents a modification of the von Auwers rearrangement and proceeds by a radical chain mechanism. The intermediate alkoxycarbonyl radical can be intercepted allowing further useful synthetic variations.