A NEW 1-ALKOXY-2-(CHALCOGENO)ALLYLIC OR 1-ALKOXY-2,4-BIS(CHALCOGENO)PENTA-2,4-DIENYL CATION - HIGHLY-REGIOSELECTIVE ALLYLATING OR PENTA-2,4-DIENYLATING ELECTROPHILES AND THEIR REACTIONS

Authors
YOSHIMATSU M GOTOH S IKEDA K KOMORI M
Citation
M. Yoshimatsu et al., A NEW 1-ALKOXY-2-(CHALCOGENO)ALLYLIC OR 1-ALKOXY-2,4-BIS(CHALCOGENO)PENTA-2,4-DIENYL CATION - HIGHLY-REGIOSELECTIVE ALLYLATING OR PENTA-2,4-DIENYLATING ELECTROPHILES AND THEIR REACTIONS, Journal of organic chemistry, 63(19), 1998, pp. 6619-6624
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
19
Year of publication
1998
Pages
6619 - 6624
Database
ISI
SICI code
0022-3263(1998)63:19<6619:AN1O1>2.0.ZU;2-7
Abstract
2-(Chalcogeno)-1-ethoxyallylic cations 4A are easily generated from th e reactions of 2-(chalcogeno)-1-ethoxyprop-1-en-3-ols 2a-e or 2-(chalc ogeno)prop-2-enal acetals 3a-c and TMSOTf and reacted with various nuc leophiles to give the adducts 5a-8a, 5b-11b, and 5c-e regio and stereo selectively. 2,4-Bis(chalcogeno)penta-2,4-dienal acetals 16a,c and the 2,4,6-tris(phenylthio)hepta-2,4,6-trienal acetal 20c also gave the di enones 17a,c and 21c in good yields. Furthermore, the intramolecular c yclization of the alkenyl alcohols 25a,b and the 2,4-dienal 2,4-dinitr ophenyl hydrazones 29a-c afforded the tetrahydrofurans 26a,b and 3,5-b is(chalcogeno)pyridines 30a-c, respectively.