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Hydrolytic selenoxide elimination reaction for the preparation of 2-chloro-1-olefins

โœ Scribed by Lars Engman

Book ID
104227511
Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
275 KB
Volume
28
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

2-Chloro-I-olefins were synthesized in a regiocontrolled way from terminal olefins by a sequence involving Markownikoff-addition of PhSeCl, chlorination of the resulting R-chloroalkyl phenyl selenides with SO Cl and, after recrystallization, hydrolysis/ selenoxide elimination in d two-phase sys * 2 em.

Vinyl chlorides are becoming increasingly important building blocks for synthetic organic chemists. By Lewis-acid assisted hydrolysis they can be mildly converted to carbonyl compounds.l They have also recently been shown to undergo metal promoted homocoupling to give

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โœ Ottorino De Lucchi; Sergio Cossu ๐Ÿ“‚ Article ๐Ÿ“… 1998 ๐Ÿ› John Wiley and Sons ๐ŸŒ English โš– 228 KB

1,4-benzodithiin 1,1,4,4-tetraoxide 11 is a reactive Upon reductive desulfonylation with sodium amalgam, the latter are transformed to tetrasubstituted polycyclic olefins dienophile that forms Diels-Alder adducts with a number of dienes. Adducts 17a-j undergo facile dehydrochlorination to 24-27. The