Nucleophilic addition of phosphine to 4-chlorostyrenes in the KOH-DMSO system

In the superbasic system KOH-DMSO (H 2 O) at 60–75 °C (2–2.5 h, atmospheric pressure), 4-chlorostyrene and 4-chloro-α-methylstyrene add phosphine at the double bond to form 1: 1 and 2: 1 anti-Markovnikov adducts in 10–18% and 58–67% yields, respectively.

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Bibliographic Details
Published inRussian chemical bulletin Vol. 62; no. 11; pp. 2495 - 2497
Main Authors Artem’ev, A. V., Malysheva, S. F., Gusarova, N. K., Korocheva, A. O., Timokhina, L. V., Trofimov, B. A.
Format Journal Article
LanguageEnglish
Published Boston Springer US 01.11.2013
Subjects
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Full Articles
Inorganic Chemistry
Organic Chemistry
superbasic medium
alkyl-phosphines
phosphine
hydrophosphination
nucleophilic addition
4-chlorostyrenes
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Summary:In the superbasic system KOH-DMSO (H 2 O) at 60–75 °C (2–2.5 h, atmospheric pressure), 4-chlorostyrene and 4-chloro-α-methylstyrene add phosphine at the double bond to form 1: 1 and 2: 1 anti-Markovnikov adducts in 10–18% and 58–67% yields, respectively.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-013-0361-1