NotesUnfortunately, these problems will always plague stereochemical studies of the pinacol rearrangement.
Experimental SectionThe compounds discussed in this paper, 1-5, have been reported elsewhere: 1 and 2,4 3,6 4,6 5.8 Comparison of physical constants with those reported as well as the agreement of infrared and nmr spectra with the assigned structures confirmed the identity of the products.General Procedure for Pinacol Rearrangement.-The glycol (0.1 g) was stirred with 5 ml of concentrated sulfuric acid. After 10 min the reaction mixture was poured into ice and water. The resulting aqueous solution was immediately extracted with methylene chloride, and the extracts were washed with 10% bicarbonate solution. The crude product was analyzed by analytical glc (6 ft X 6 mm glass column, packed with 16% hyprose SP 80 on 60-68 mesh Chromosorb W).The spiranone 3 and the epoxide 5 were subjected to the same reaction conditions and work-up.
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