- Preparation of Some Oxa- and Thia-decalins and -propellanes. Barriers to Conformational Interconversion
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Reactions of 5,6-dihydro-2,3-dimethyl-1,4-dioxin, -1,4-oxathiin and -1,4-dithiin with bromine in the presence of 1,2-ethanediol, 2-mercaptoethanol and 1,2-ethanedithiol, respectively, afforded, in most cases, high yields of the corresponding oxa- and thia-decalins as cis-isomers only.Similar reactions of the bicyclic dihydrodioxins, 2,5-dioxabicyclodec-1(6)-ene and the sulfur analogues gave the corresponding propellanes in high yields.The barriers to conformational interconversion were obtained from variable temperature NMR spectra.Other examples of propellanes were obtained; addition of dihalocarbenes to the bicyclic dihydrodioxins furnished the corresponding dihalocyclopropane derivatives, and the photochemical addition of benzophenone gave the expected oxetane.
- Fjeldskaar, Inger Reidun,Skatteboel, Lars
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p. 410 - 417
(2007/10/02)
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