1,3-DICHLOROPROPENE AS A SOURCE OF THE 1,3-DIANION DERIVED FROM PROPENE - SYNTHESIS OF UNSATURATED 1,5-DIOLS AND DIHYDROPYRANS

Authors
GUIJARRO A YUS M
Citation
A. Guijarro et M. Yus, 1,3-DICHLOROPROPENE AS A SOURCE OF THE 1,3-DIANION DERIVED FROM PROPENE - SYNTHESIS OF UNSATURATED 1,5-DIOLS AND DIHYDROPYRANS, Tetrahedron, 50(46), 1994, pp. 13269-13276
Citations number
42
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
46
Year of publication
1994
Pages
13269 - 13276
Database
ISI
SICI code
0040-4020(1994)50:46<13269:1AASOT>2.0.ZU;2-2
Abstract
The reaction of 1,3-dichloropropene (1, ca. 1/1 Z/E mixture) with an e xcess of lithium powder and a catalytic amount of 4,4'-di-tert-butylbi phenyl (DTBB, 5 mol %) in the presence of an electrophile [Me(2)CO, Et (2)CO, (CH2)(4)CO, (CH2)(5)CO, Bu(t)CHO, Me(3)SiCl] in THF at 0 degree s C affords, after hydrolysis with water, the expected unsaturated 1,5 -diols 3 as a Z/E mixture or disilane (E)-4. Treatment of isolated com pounds (Z)-3 with 85% phosphoric acid gives the expected dihydropyrans 5.