Stereochemical labeling at natural abundance. Stereochemistry, isotope effects, and mechanism of the Diels-Alder reaction of hexachlorocyclopentadiene with ethyl vinyl ether

Daniel A. Singleton; Steven R. Merrigan; Allen A. Thomas

doi:10.1016/S0040-4039(98)02508-8

Stereochemical labeling at natural abundance. Stereochemistry, isotope effects, and mechanism of the Diels-Alder reaction of hexachlorocyclopentadiene with ethyl vinyl ether

Daniel A. Singleton, Steven R. Merrigan, Allen A. Thomas

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

11 Scopus citations

Abstract

The variation in cis versus trans deuterium content in natural-abundance ethyl vinyl ether is retained in its cycloadduct with hexachloroeyclopentadiene, indicative of a stereospecific process. The kinetic isotope effects for this reaction were also determined at natural abundance, and suggest a very asynchronous but concerted process. This conclusion is backed by comparison with theoretically calculated isotope effects.

Original language	English (US)
Pages (from-to)	639-642
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	4
DOIs	https://doi.org/10.1016/S0040-4039(98)02508-8
State	Published - Jan 22 1999
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(98)02508-8

Cite this

@article{7a7df24d1c8943418c586e8c65b9919e,

title = "Stereochemical labeling at natural abundance. Stereochemistry, isotope effects, and mechanism of the Diels-Alder reaction of hexachlorocyclopentadiene with ethyl vinyl ether",

abstract = "The variation in cis versus trans deuterium content in natural-abundance ethyl vinyl ether is retained in its cycloadduct with hexachloroeyclopentadiene, indicative of a stereospecific process. The kinetic isotope effects for this reaction were also determined at natural abundance, and suggest a very asynchronous but concerted process. This conclusion is backed by comparison with theoretically calculated isotope effects.",

author = "Singleton, {Daniel A.} and Merrigan, {Steven R.} and Thomas, {Allen A.}",

note = "Funding Information: Acknowledgment. We thank NIH grant # GM-45617 and The Robert A. Welch Foundation for support of this research.",

year = "1999",

month = jan,

day = "22",

doi = "10.1016/S0040-4039(98)02508-8",

language = "English (US)",

volume = "40",

pages = "639--642",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "4",

}

TY - JOUR

T1 - Stereochemical labeling at natural abundance. Stereochemistry, isotope effects, and mechanism of the Diels-Alder reaction of hexachlorocyclopentadiene with ethyl vinyl ether

AU - Singleton, Daniel A.

AU - Merrigan, Steven R.

AU - Thomas, Allen A.

N1 - Funding Information: Acknowledgment. We thank NIH grant # GM-45617 and The Robert A. Welch Foundation for support of this research.

PY - 1999/1/22

Y1 - 1999/1/22

N2 - The variation in cis versus trans deuterium content in natural-abundance ethyl vinyl ether is retained in its cycloadduct with hexachloroeyclopentadiene, indicative of a stereospecific process. The kinetic isotope effects for this reaction were also determined at natural abundance, and suggest a very asynchronous but concerted process. This conclusion is backed by comparison with theoretically calculated isotope effects.

AB - The variation in cis versus trans deuterium content in natural-abundance ethyl vinyl ether is retained in its cycloadduct with hexachloroeyclopentadiene, indicative of a stereospecific process. The kinetic isotope effects for this reaction were also determined at natural abundance, and suggest a very asynchronous but concerted process. This conclusion is backed by comparison with theoretically calculated isotope effects.

UR - http://www.scopus.com/inward/record.url?scp=0033593307&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033593307&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(98)02508-8

DO - 10.1016/S0040-4039(98)02508-8

M3 - Article

AN - SCOPUS:0033593307

SN - 0040-4039

VL - 40

SP - 639

EP - 642

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 4

ER -

Stereochemical labeling at natural abundance. Stereochemistry, isotope effects, and mechanism of the Diels-Alder reaction of hexachlorocyclopentadiene with ethyl vinyl ether

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this