One-Pot Iodosulfonylation Dehydroiodination of Alkenes: (E)-beta-Tosylstyrene: An Experiment for Undergraduate Organic Chemistry Laboratory

Carmen Nájera , José M. Sansano and Miguel Yus
Departamento de Quimica Organica, Universidad de Alicancante, Apdo. 99, E-03080 Alicante, Spain
J. Chem. Educ., 1995, 72 (7), p 664
DOI: 10.1021/ed072p664
Publication Date: July 1995

Abstract

The iodosulfonylation of styrene with sodium p-toluenesulfinate and iodine in methanol followed by dehydroiodination with IN methanolic potassium hydroxide to give regioand stereoselectively (E)-beta-tosylstyrene in >80% yield is described. This one-pot procedure is an adequate experiment for Undergraduate Organic Chemistry Laboratory.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Free Radicals
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  • Received: August 03, 2009

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