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Paper | Special issue | Vol 47, No. 2, 1998, pp.793-809
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)80
X-Ray Crystallographic Analysis of 2,5-Bis(diphenylmethylsilyl)thiophene Monooxide and the Diels-Alder Reaction of Thiophene Monooxide with Dienophiles

Naomichi Furukawa,* Shao-Zhong Zhang, Ernst Horn, Ohgi Takahashi, Soichi Sato, Masataka Yokoyama, and Kentaro Yamaguchi

*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan

Abstract

X-Ray crystallographic analysis of 2,5-his(diphenylmethylsilyl)thiophene monooxide revealed that the thiophene ring is not a planar structure and that the S-O bond is tilted ca. 14° out of the ring plane. The Diels-Alder reaction of 2,5-bis(trimethylsilyl)thiophene with dienophiles gave the adducts in high yields. The stereochemical courses for the reactions are exclusively endo-orientation and syn-direction with respect to the S-O bond. This stereochemistry agrees with the results obtained from RHF and MP2 MO calculations using the 6-31G(*) basis set.