Methoxycarbonyl migration in 3-methylene-1,4-cyclohexadienes. An extension of the von Auwers rearrangement
- Resource Type
- Authors
- Samir Z. Zard; Raphael F. Guignard; Mehdi Boumediene
- Source
- Tetrahedron
Tetrahedron, Elsevier, 2016, 72 (26), pp.3678-3686 ⟨10.1016/j.tet.2016.03.032⟩
- Subject
- 010405 organic chemistry
Chemistry
Stereochemistry
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Organic Chemistry
Cyclohexadienes
Substituent
Aromatization
010402 general chemistry
01 natural sciences
Biochemistry
0104 chemical sciences
chemistry.chemical_compound
Drug Discovery
Methylene
- Language
- English
- ISSN
- 0040-4020
International audience; 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.