Rearrangement of methylenecamphor during electrophilic bromination: Remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system

Allen A. Thomas; Keith A. Monk; Sonia Abraham; Stella Lee; Charles M. Garner

doi:10.1016/S0040-4039(01)00089-2

Rearrangement of methylenecamphor during electrophilic bromination: Remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system

Allen A. Thomas, Keith A. Monk, Sonia Abraham, Stella Lee, Charles M. Garner

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

Treatment of (+)-methylenecamphor (2) with NBS in the presence of pyridine resulted in a rapid and remarkably clean rearrangement to yield a brominated (+)-methylenefenchone (3) in high yield and purity (>96%). The structure of the product was established by X-ray crystallography and the stereochemistry confirmed by both polarimetric and chiral GC analyses. Two transformations of the product were also performed to elucidate the structure.

Original language	English (US)
Pages (from-to)	2261-2263
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	12
DOIs	https://doi.org/10.1016/S0040-4039(01)00089-2
State	Published - Mar 18 2001
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Rearrangement of methylenecamphor during electrophilic bromination: Remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system",

abstract = "Treatment of (+)-methylenecamphor (2) with NBS in the presence of pyridine resulted in a rapid and remarkably clean rearrangement to yield a brominated (+)-methylenefenchone (3) in high yield and purity (>96%). The structure of the product was established by X-ray crystallography and the stereochemistry confirmed by both polarimetric and chiral GC analyses. Two transformations of the product were also performed to elucidate the structure.",

author = "Thomas, {Allen A.} and Monk, {Keith A.} and Sonia Abraham and Stella Lee and Garner, {Charles M.}",

note = "Funding Information: This work was supported in part by the Robert A. Welch Foundation. Helpful discussions with David Minter (Texas Christian University) are gratefully acknowledged.",

year = "2001",

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doi = "10.1016/S0040-4039(01)00089-2",

language = "English (US)",

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T1 - Rearrangement of methylenecamphor during electrophilic bromination

T2 - Remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system

AU - Thomas, Allen A.

AU - Monk, Keith A.

AU - Abraham, Sonia

AU - Lee, Stella

AU - Garner, Charles M.

N1 - Funding Information: This work was supported in part by the Robert A. Welch Foundation. Helpful discussions with David Minter (Texas Christian University) are gratefully acknowledged.

PY - 2001/3/18

Y1 - 2001/3/18

N2 - Treatment of (+)-methylenecamphor (2) with NBS in the presence of pyridine resulted in a rapid and remarkably clean rearrangement to yield a brominated (+)-methylenefenchone (3) in high yield and purity (>96%). The structure of the product was established by X-ray crystallography and the stereochemistry confirmed by both polarimetric and chiral GC analyses. Two transformations of the product were also performed to elucidate the structure.

AB - Treatment of (+)-methylenecamphor (2) with NBS in the presence of pyridine resulted in a rapid and remarkably clean rearrangement to yield a brominated (+)-methylenefenchone (3) in high yield and purity (>96%). The structure of the product was established by X-ray crystallography and the stereochemistry confirmed by both polarimetric and chiral GC analyses. Two transformations of the product were also performed to elucidate the structure.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Rearrangement of methylenecamphor during electrophilic bromination: Remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system

Abstract

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