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

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

doi:10.1016/S0040-4039(97)10092-2

Rearrangement pathways of the tricyclo[4.1.0.0^1,3]heptyl skeleton

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

Chemistry (Twin Cities)

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Abstract

Syn- and anti-1-methyltricyclo[4.1.0.0^4,6]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[4.1.0.0^3,5]heptane (7), the product of a solvent trapped cyclopropyl cation.

Original language	English (US)
Pages (from-to)	7819-7822
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	45
DOIs	https://doi.org/10.1016/S0040-4039(97)10092-2
State	Published - Nov 10 1997

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

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.",

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AU - Dombrowski, Gary W.

AU - Gassman, Paul G.

AU - Kass, Steven R.

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N2 - 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.

AB - 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.

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Rearrangement pathways of the tricyclo[4.1.0.0^1,3]heptyl skeleton

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