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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 179, 2004 - Issue 8
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Original Articles

TRIFLUOROMETHYLTHIOLATION OF NORBORNENE

S. Munavalli Geo-Centers, Inc., Gunpowder Branch, APG
,
R. K. Rohrbaugh U.S. Army, Edgewood Chemical Biological Center, APG, Maryland, USA
,
G. W. Wagner U.S. Army, Edgewood Chemical Biological Center, APG, Maryland, USA
,
H. D. Durst U.S. Army, Edgewood Chemical Biological Center, APG, Maryland, USA
&
F. R. Longo Geo-Centers, Inc., Gunpowder Branch, APG
Pages 1635-1643 | Received 01 Dec 2003, Accepted 01 Dec 2003, Published online: 16 Aug 2010
 
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Abstract

Treatment of norbornene with trifluoromethylsulfenyl chloride at −80°C furnishes, in addition to trifluoromethylthionortricyclane, four isomeric (chloro) (trifluoromethylthio)-norbornanes and bis-(2, 6-trifluoromethylthio)norbornane. The probable mechanism of the formation of the various compounds via free radical intermediates and their mass spectral characterization are described in this communication.

Notes

Compounds 6 and 8 co-elute and together form 2% of the yield.

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