Rearrangements of 3-heterobicyclo[3.2.0]hept-6-enes |
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Authors: | Arthur G Schultz Theodore H Fedynyshyn |
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Institution: | Department of Chemistry, Rensselaer Polytechnic Institute, Troy, NY 12181, U.S.A. |
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Abstract: | Studies directed at a synthesis of dihydrothiepin 1b have resulted in the elucidation of several factors which effect cyclobutene ring opening in the 3-heterobicyclo3.2.0]hept-6-ene ring system. We report the unexpected rearrangement of 4a, 4b, 13b and 13c to the synthetically useful a-vinyl-2,5-dihydrothiophenes 7a, 7b, 15a and 15b, respectively. Conversion of 4a to 6 is suggested to occur by a 1,3-rearrangement of 4a to isomeric 3-thiabicyclo3.2.0]hept-6-ene 19 followed by cyclobutene ring opening in 19. |
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