Rearrangement pathways of the tricyclo[4.1.0.01,3]heptyl skeleton

Gary W. Dombrowski, Paul G. Gassman, Steven R. Kass

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Syn- and anti-1-methyltricyclo[4.1.0.04,6]heptan-2-ol derivatives (4a and 4b) have been prepared. Their buffered solvolyses in anhydrous 2,2,2- trifluoroethanol were studied. Anti dinitrobenzoate 4a solvolyzes to give mainly m-xylene and two trifluoroethyl ethers (5 and 6). Solvolysis of the syn mesylate 4b gives 6-methyl-1-(2,2,2- trifluoroethoxy)tricyclo[4.1.0.03,5]heptane (7), the product of a solvent trapped cyclopropyl cation.

Original languageEnglish (US)
Pages (from-to)7819-7822
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number45
DOIs
StatePublished - Nov 10 1997

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