Ring closure of 2-thia- and 2-sulfonyl-5-hexenyl radicals

E. W. Della; S. D. Graney

doi:10.1016/S0040-4039(00)01377-0

Ring closure of 2-thia- and 2-sulfonyl-5-hexenyl radicals

E. W. Della, S. D. Graney

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

18 Citations (Scopus)

Abstract

Reductive cyclisation of the 2-sulfonyl-5-hexenyl radical with tributyltin hydride in benzene at 80°C affords a 73:23 mixture of the sulfones derived from 5-exo- and 6-endo- ring closure with a small quantity (4%) of reduced material; under identical conditions, the 2-thia-5-hexenyl radical gives a 70:13:17 mixture of the corresponding sulfides. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	7987-7990
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	41
DOIs	https://doi.org/10.1016/S0040-4039(00)01377-0
Publication status	Published - 7 Oct 2000

Keywords

Heterocyclic synthesis
Radical cyclisation
α-sulfonyl radicals
α-thia radicals

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abstract = "Reductive cyclisation of the 2-sulfonyl-5-hexenyl radical with tributyltin hydride in benzene at 80°C affords a 73:23 mixture of the sulfones derived from 5-exo- and 6-endo- ring closure with a small quantity (4%) of reduced material; under identical conditions, the 2-thia-5-hexenyl radical gives a 70:13:17 mixture of the corresponding sulfides. (C) 2000 Elsevier Science Ltd.",

keywords = "Heterocyclic synthesis, Radical cyclisation, α-sulfonyl radicals, α-thia radicals",

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T1 - Ring closure of 2-thia- and 2-sulfonyl-5-hexenyl radicals

AU - Della, E. W.

AU - Graney, S. D.

PY - 2000/10/7

Y1 - 2000/10/7

N2 - Reductive cyclisation of the 2-sulfonyl-5-hexenyl radical with tributyltin hydride in benzene at 80°C affords a 73:23 mixture of the sulfones derived from 5-exo- and 6-endo- ring closure with a small quantity (4%) of reduced material; under identical conditions, the 2-thia-5-hexenyl radical gives a 70:13:17 mixture of the corresponding sulfides. (C) 2000 Elsevier Science Ltd.

AB - Reductive cyclisation of the 2-sulfonyl-5-hexenyl radical with tributyltin hydride in benzene at 80°C affords a 73:23 mixture of the sulfones derived from 5-exo- and 6-endo- ring closure with a small quantity (4%) of reduced material; under identical conditions, the 2-thia-5-hexenyl radical gives a 70:13:17 mixture of the corresponding sulfides. (C) 2000 Elsevier Science Ltd.

KW - Heterocyclic synthesis

KW - Radical cyclisation

KW - α-sulfonyl radicals

KW - α-thia radicals

UR - http://www.scopus.com/inward/record.url?scp=0034619154&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)01377-0

DO - 10.1016/S0040-4039(00)01377-0

M3 - Article

AN - SCOPUS:0034619154

SN - 0040-4039

VL - 41

SP - 7987

EP - 7990

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 41

ER -

Ring closure of 2-thia- and 2-sulfonyl-5-hexenyl radicals

Abstract

Keywords

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