Homolytic and conjugate addition of thiols to 2,4-dimethyl-2-vinyl-1,3-dioxa-2-silacyclohexane

Authors
Makaeva, RM Zorin, VV Musavirov, RR Brod'ko, LS Gvozdik, SV Musavirov, RS
Citation
Rm. Makaeva et al., Homolytic and conjugate addition of thiols to 2,4-dimethyl-2-vinyl-1,3-dioxa-2-silacyclohexane, RUSS J ORG, 37(3), 2001, pp. 442-445
Citations number
9
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
10704280 → ACNP
Volume
37
Issue
3
Year of publication
2001
Pages
442 - 445
Database
ISI
SICI code
1070-4280(200103)37:3<442:HACAOT>2.0.ZU;2-R
Abstract
Homolytic reaction of 1-propane- and 1-pentanethiols to 2,4-dimethyl-2-viny l-1,3-dioxa-2-silacyclohexane, initiated by di-tert-butyl peroxide at 130 d egreesC, yields a mixture of isomeric sulfides (95%) as a result of additio n at the alpha- and beta -positions of the vinyl group. Conjugate addition of alkanethiols in the presence of the corresponding sodium thiolate at 100 degreesC gives 10% of the same alpha- and beta -regioisomeric sulfides at a ratio of I : 20.