ALLENYL ALLYLIC ETHERS - SYNTHESIS AND THERMAL REARRANGEMENTS

Authors
DULCERE JP CRANDALL J FAURE R SANTELLI M AGATI V MIHOUBI MN
Citation
Jp. Dulcere et al., ALLENYL ALLYLIC ETHERS - SYNTHESIS AND THERMAL REARRANGEMENTS, Journal of organic chemistry, 58(21), 1993, pp. 5702-5708
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
58
Issue
21
Year of publication
1993
Pages
5702 - 5708
Database
ISI
SICI code
0022-3263(1993)58:21<5702:AAE-SA>2.0.ZU;2-1
Abstract
Application of the sequence halogenation/dehydrohalogenation/isomeriza tion to alkenes 1a-g affords allenyl allylic ethers 5a-g. Thermal isom erizations of 5a,d,e proceed by Claisen rearrangement, while 5b,c,f,g are transformed by alternate modes of [2 + 2]cycloaddition involving b iradical intermediates of type 19 to polycyclic structures; the variat ions in these thermal isomerizations are mainly a function of ring siz e.