On the stereoisomerization of radicals during aliphatic nucleophilic substitutions

Kim Daasbjerg; Torben Lund; Henning Lund

doi:10.1016/S0040-4039(00)95237-7

On the stereoisomerization of radicals during aliphatic nucleophilic substitutions

Kim Daasbjerg^*, Torben Lund, Henning Lund

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Bornyl and isobornyl bromide react with an enolate ion 1^- to the same products which indicates a stereoisomerization during the aliphatic nucleophilic substitution. Substitution of 1^- with a "radical clock" suggests a radical coupling within the solvent cage. Reaction between a radical clock and anion radicals suggests in this case a coupling outside the solvent cage.

Original language	English
Journal	Tetrahedron Letters
Volume	30
Issue number	4
Pages (from-to)	493-496
Number of pages	4
ISSN	0040-4039
DOIs	https://doi.org/10.1016/S0040-4039(00)95237-7
Publication status	Published - 1989
Externally published	Yes

Link to document

10.1016/S0040-4039(00)95237-7

Cite this

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title = "On the stereoisomerization of radicals during aliphatic nucleophilic substitutions",

abstract = "Bornyl and isobornyl bromide react with an enolate ion 1- to the same products which indicates a stereoisomerization during the aliphatic nucleophilic substitution. Substitution of 1- with a {"}radical clock{"} suggests a radical coupling within the solvent cage. Reaction between a radical clock and anion radicals suggests in this case a coupling outside the solvent cage.",

author = "Kim Daasbjerg and Torben Lund and Henning Lund",

year = "1989",

doi = "10.1016/S0040-4039(00)95237-7",

language = "English",

volume = "30",

pages = "493--496",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Pergamon Press",

number = "4",

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TY - JOUR

T1 - On the stereoisomerization of radicals during aliphatic nucleophilic substitutions

AU - Daasbjerg, Kim

AU - Lund, Torben

AU - Lund, Henning

PY - 1989

Y1 - 1989

N2 - Bornyl and isobornyl bromide react with an enolate ion 1- to the same products which indicates a stereoisomerization during the aliphatic nucleophilic substitution. Substitution of 1- with a "radical clock" suggests a radical coupling within the solvent cage. Reaction between a radical clock and anion radicals suggests in this case a coupling outside the solvent cage.

AB - Bornyl and isobornyl bromide react with an enolate ion 1- to the same products which indicates a stereoisomerization during the aliphatic nucleophilic substitution. Substitution of 1- with a "radical clock" suggests a radical coupling within the solvent cage. Reaction between a radical clock and anion radicals suggests in this case a coupling outside the solvent cage.

U2 - 10.1016/S0040-4039(00)95237-7

DO - 10.1016/S0040-4039(00)95237-7

M3 - Journal article

AN - SCOPUS:0012714865

SN - 0040-4039

VL - 30

SP - 493

EP - 496

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 4

ER -