Journal of Organic Chemistry p. 3098 - 3104 (1988)
Update date:2022-08-02
Topics:
Takahashi, Kimio
Shiro, Motoo
Kishi, Morio
Reaction of 1,3-dibromo-4-phenylcyclopentane (23), prepared from 4-hydroxycyclopent-2-en-1-one (10) in a stereocontrolled manner, or its stereoisomer 24 with anhydrous hydrogen peroxide in the presence of silver trifluoroacetate in ether gave 1-phenyl-2,3-dioxabicyclo<2.2.1>heptane (25) mainly as a rearranged product.The expected 5-phenyl-2,3-dioxabicyclo<2.2.1>heptane (8) and phenylcyclopentenyl hydroperoxides 26 and 27 were also formed in this reaction.An authentic sample of endoperoxide 8 was prepared by using peroxide transfer reaction between bis(tri-n-butyltin)peroxide and bistriflate of cis-diol 35.The stereochemistry of the endoperoxide 8 and related compounds in this series was confirmed by correlation with the data from X-ray crystallographic analysis of the diacetate of diol 21 obtained from endoperoxide 8 by stannous chloride reduction.
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