Synthesis of 2-fluoro-3-phenylthio-1,3-butadiene and 2-trifluoromethyl-3-phenylthio-1,3-butadiene and their reactivities toward various dienophiles

Paul Kamaldeep; Ji Hye Hwang; Ji Hoon Choi; In Howa Jeong

doi:10.1021/ol901867q

Synthesis of 2-fluoro-3-phenylthio-1,3-butadiene and 2-trifluoromethyl-3-phenylthio-1,3-butadiene and their reactivities toward various dienophiles

Org Lett. 2009 Oct 15;11(20):4728-31. doi: 10.1021/ol901867q.

Authors

Paul Kamaldeep¹, Ji Hye Hwang, Ji Hoon Choi, In Howa Jeong

Affiliation

¹ Department of Chemistry and Medical Chemistry, Yonsei University, Wonju 220-710, Korea.

PMID: 19778005
DOI: 10.1021/ol901867q

Abstract

A general approach for the synthesis of novel 2-fluoro-3-phenylthio-1,3-butadiene (8) and 2-trifluoromethyl-3-phenylthio-1,3-butadiene (9) from monobromoalkene and dibromoalkenes has been developed. Subsequent Diels-Alder reactions of these dienes with symmetrical and unsymmetrical dienophiles in the presence of Lewis acids gave a variety of fluorinated six-membered carbocycles in moderate to high yields.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Butadienes / chemical synthesis*
Butadienes / chemistry
Halogenation
Hydrogen-Ion Concentration
Sulfides / chemical synthesis*
Sulfides / chemistry

Substances

2-fluoro-3-phenylthio-1,3-butadiene
2-trifluoromethyl-3-phenylthio-1,3-butadiene
Butadienes
Sulfides