E. Kosower, B. Pazhenchevsky, D. Marciano
Sep 1, 1990
Citations
0
Influential Citations
9
Citations
Journal
Journal of the American Chemical Society
Abstract
Conversion of the dibromo compound, 4,6-bis(bromomethyl)-3,7-dimethyl- 1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione (syn-(BrCH 2 ,CH 3 )B) or the related 3,7-dichloro derivative (syn-(BrCH 2 ,Cl)B) to a 4,6-sulfone-bridged bimane via oxidation of a 4,6-thiatrimethylene derivative is described. Elimination of SO 2 via thermolysis of the sulfones at 525 o C in a quartz reactor yields the strained tricyclic bimanes containing a 4,6-dimethylene group («zero-bridge») μ-0-syn-(CH 2 ,CH 3 )B (3e) and μ-0-syn-(CH 2 ,Cl)B (3a)