A GENERAL-METHOD FOR THE SYNTHESIS OF 2-ALKYL SUBSTITUTED 1,3-DIENES STARTING FROM 2-(CHLOROMETHYL)-3-TOSYLPROPENE

Authors
NAJERA C SANSANO JM
Citation
C. Najera et Jm. Sansano, A GENERAL-METHOD FOR THE SYNTHESIS OF 2-ALKYL SUBSTITUTED 1,3-DIENES STARTING FROM 2-(CHLOROMETHYL)-3-TOSYLPROPENE, Tetrahedron, 50(19), 1994, pp. 5829-5844
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
19
Year of publication
1994
Pages
5829 - 5844
Database
ISI
SICI code
0040-4020(1994)50:19<5829:AGFTSO>2.0.ZU;2-L
Abstract
The alkylation of the monolithium derived 5 of 2-(chloromethyl)-3-tosy lpropene (1) with bromo- or iodo-methyltrimethylsilane affords the bet a-silyl sulfone 7, which after nucleophilic substitution of the chlori ne atom followed by beta-elimination of tosyltrimethylsilane, promoted by tetrabutylammonium fluoride (TBAF), gives 2-substituted conjugated dienes 6 and the outer-ring diene 14. Racemic ipsenol (10b), an aggre gation pheromone of the bark beetle Ips paraconfusus Lanier, is prepar ed.