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Letter

Chloromethanesulfonylethene and Dichloromethanesulfonylethene: New Reagents for Tandem Diels−Alder/Ramberg−Bäcklund Reactions

Supporting Info

Eric Block,* Hak Rim Jeon, Shao-Zhong Zhang, and Evgeny V. Dikarev

Department of Chemistry, State University of New York at Albany, Albany, New York 12222

Org. Lett., 2004, 6 (3), pp 437–440

DOI: 10.1021/ol0363523

Publication Date (Web): January 14, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, eb801@albany.edu

Abstract

Chloromethanesulfonylethene (3a) and dichloromethanesulfonylethene (3b) were prepared by oxidation of the adducts of ethylene and ClCH₂SCl or Cl₂CHSCl, respectively, followed by NaHCO₃ dehydrochlorination. With dienes, 3a gave Diels−Alder adducts that, with base, underwent Ramberg−Bäcklund reaction, giving products corresponding to the adducts of the dienes and allene. Similarly, 3b gave Diels−Alder adducts that, with base in the presence of the novel chlorine source MeSO₂CCl₃, cleanly afforded products corresponding to the adducts of the dienes and 1,1-dichloropropa-1,2-diene.

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