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 journalArticle

3 Citations (Scopus)

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

Fingerprint

Trifluoroethanol
Heptanes
Mesylates
Ethers
Skeleton
Cations
Derivatives
3-xylene

Cite this

Rearrangement pathways of the tricyclo[4.1.0.01,3]heptyl skeleton. / Dombrowski, Gary W.; Gassman, Paul G.; Kass, Steven R.

In: Tetrahedron Letters, Vol. 38, No. 45, 10.11.1997, p. 7819-7822.

Research output: Contribution to journalArticle

Dombrowski, Gary W. ; Gassman, Paul G. ; Kass, Steven R. / Rearrangement pathways of the tricyclo[4.1.0.01,3]heptyl skeleton. In: Tetrahedron Letters. 1997 ; Vol. 38, No. 45. pp. 7819-7822.
@article{9b4e1b8f5b5647d2a6c7597b35ffcdef,
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.",
author = "Dombrowski, {Gary W.} and Gassman, {Paul G.} and Kass, {Steven R}",
year = "1997",
month = "11",
day = "10",
doi = "10.1016/S0040-4039(97)10092-2",
language = "English (US)",
volume = "38",
pages = "7819--7822",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "45",

}

TY - JOUR

T1 - Rearrangement pathways of the tricyclo[4.1.0.01,3]heptyl skeleton

AU - Dombrowski, Gary W.

AU - Gassman, Paul G.

AU - Kass, Steven R

PY - 1997/11/10

Y1 - 1997/11/10

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.

UR - http://www.scopus.com/inward/record.url?scp=0030773525&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030773525&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(97)10092-2

DO - 10.1016/S0040-4039(97)10092-2

M3 - Article

VL - 38

SP - 7819

EP - 7822

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 45

ER -