Difunctionalized Brendanes via Thallium Triacetate Cleavage of the Cyclopropyl Ring of Triaxane

Douglas F. Covey, Alex Nickon

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Abstract

The reaction of triaxane with thallium triacetate in acetic acid gave a 90% yield of a diacetate mixture which con-tained 2-(a)-acetoxy-4-(e)-acetoxynoradamantane, 2, 4-di-(e)-diacetoxynoradamantane, and 4-exo-acetoxy-8-anti-acetoxybrendane in the ratio 3:15:82. The preponderant diacetate was isolated from the mixture in 43% yield. This reaction provides a simple synthetic route to previously unreported C-8 functionalized brendane derivatives. A structure proof for the brendyl diacetate is presented together with analytical and spectroscopic evidence for the two noradamantyl diacetates. The lead tetraacetate cleavage of triaxane was also investigated and found by GLC analysis to produce 2-acetoxytriaxane, an unidentified component, 2-acetoxynoradamantane, 2-(a)-acetoxy-4-(e)-acetoxynoradamantane, 2, 4-di-(e)-diacetoxynoradamantane, and 4-exo-acetoxy-8-anti-acetoxybrendane in the ratio of 72:1:8:<1:2:17.

Original languageEnglish
Pages (from-to)794-799
Number of pages6
JournalJournal of Organic Chemistry
Volume42
Issue number5
DOIs
StatePublished - 1977

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