92231-57-7Relevant articles and documents
Studies of Chrysanthemic Acid Derivatives: Catalyses Reactions of 3-(2-Hydroxymethyl-3,3-dimethylcyclopropyl)-2-methylpropanol and Formation of a Novel Eight-membered Cyclic Sulphite
Crammer, Bernard,Goldschmidt, Zeev,Ikan, Raphael,Cohen, Shmuel
, p. 887 - 891 (2007/10/02)
Acid catalysed reaction of the cyclopropanediol (3) derived from cis-chrysanthemic acid cis-(1) afforded, depending on the reaction conditions, 3-vinyl-2,2,5,5-tetramethyltetrahydrofuran (4) and 4,4,7,7-tetramethyl-3-oxabicycloheptane (5).On treatment with thionyl chloride-pyridine complex there was obtained in addition the eight-membered cyclic sulphite, 6,6,9,9-tetramethyl-3,5-dioxa-4-thiabicyclononane 4-oxide (6).X-Ray analysis confirms a boat-chair conformation with the S=O group trans to the cyclopropane ring in an equatorial situation.Thermal reaction of (6) gave either (4) or a mixture of (5), cis-chrysanthemol (7), and cis-isochrysanthemol (8).