ALPHA-ALKYLATION OF ALPHA,BETA-UNSATURATED ALDEHYDE DIMETHYLHYDRAZONES ACCOMPANIED WITH THE DOUBLE-BOND MIGRATION TO BETA,GAMMA

Authors
YAMASHITA M MATSUMIYA K NAKANO K
Citation
M. Yamashita et al., ALPHA-ALKYLATION OF ALPHA,BETA-UNSATURATED ALDEHYDE DIMETHYLHYDRAZONES ACCOMPANIED WITH THE DOUBLE-BOND MIGRATION TO BETA,GAMMA, Bulletin of the Chemical Society of Japan, 66(6), 1993, pp. 1759-1763
Citations number
14
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
66
Issue
6
Year of publication
1993
Pages
1759 - 1763
Database
ISI
SICI code
0009-2673(1993)66:6<1759:AOAAD>2.0.ZU;2-X
Abstract
Lithiated alpha,beta-unsaturated aldehyde N,N-dimethylhydrazones react ed with alkyl halides accompanied by double bond migration to give alp ha-alkylated beta,gamma-unsaturated aldehyde N,N-dimethylhydrazones in satisfactory yields. This reaction was found to be caused at the firs t step by deprotonation from a gamma-carbon atom by lithium diisopropy lamide. In the case of hydrazones with two kinds of gamma-protons, dep rotonation from the less hindered gamma-carbon occurred selectively. U sing this reaction, a novel sesquiterpene, 2,5,9-trimethyl-2-vinyl-4,8 -decadienal. which has a vinyl group at the alpha-position, was synthe sized in a good yield.