Alkenylthioimidoyl radicals: competition between Β-scission and cyclization to dihydrothiophen-2-ylidene-amines

M Minozzi; D Nanni; John Christopher Walton

doi:10.1021/ol034073+

Alkenylthioimidoyl radicals: competition between Β-scission and cyclization to dihydrothiophen-2-ylidene-amines

M Minozzi, D Nanni, John Christopher Walton

Research output: Other contribution

Abstract

But-3-enylthiolmidoyl radicals were shown by EPR spectroscopy and end product analysis to ring-close predominantly in the 5-exo mode with a rate constant of 2.4 x 10(4) s(-1) at 300 K to afford substituted dihydrothiophenylmethyl radicals. This ring closure was in competition with dissociation to but-3-enyl radicals and an isothiocyanate. The dissociation predominated at temperatures above ca. 300 K.

Original language	English
Volume	5
DOIs	https://doi.org/10.1021/ol034073+
Publication status	Published - 20 Mar 2003

Keywords

ENANTIOSELECTIVE TOTAL SYNTHESIS
ELECTRON-SPIN RESONANCE
(-)-ALPHA-KAINIC ACID
ARYL ISOTHIOCYANATES
ARYLIMIDOYL RADICALS
AROMATIC ANNELATION
RATE CONSTANTS
ISONITRILES
QUINOLINES
CHEMISTRY

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@misc{752f4226695f4e739d76dc8cef84e404,

title = "Alkenylthioimidoyl radicals: competition between Β-scission and cyclization to dihydrothiophen-2-ylidene-amines",

abstract = "But-3-enylthiolmidoyl radicals were shown by EPR spectroscopy and end product analysis to ring-close predominantly in the 5-exo mode with a rate constant of 2.4 x 10(4) s(-1) at 300 K to afford substituted dihydrothiophenylmethyl radicals. This ring closure was in competition with dissociation to but-3-enyl radicals and an isothiocyanate. The dissociation predominated at temperatures above ca. 300 K.",

keywords = "ENANTIOSELECTIVE TOTAL SYNTHESIS, ELECTRON-SPIN RESONANCE, (-)-ALPHA-KAINIC ACID, ARYL ISOTHIOCYANATES, ARYLIMIDOYL RADICALS, AROMATIC ANNELATION, RATE CONSTANTS, ISONITRILES, QUINOLINES, CHEMISTRY",

author = "M Minozzi and D Nanni and Walton, {John Christopher}",

note = "Org Lett",

year = "2003",

month = mar,

day = "20",

doi = "10.1021/ol034073+",

language = "English",

volume = "5",

type = "Other",

}

TY - GEN

T1 - Alkenylthioimidoyl radicals: competition between Β-scission and cyclization to dihydrothiophen-2-ylidene-amines

AU - Minozzi, M

AU - Nanni, D

AU - Walton, John Christopher

N1 - Org Lett

PY - 2003/3/20

Y1 - 2003/3/20

N2 - But-3-enylthiolmidoyl radicals were shown by EPR spectroscopy and end product analysis to ring-close predominantly in the 5-exo mode with a rate constant of 2.4 x 10(4) s(-1) at 300 K to afford substituted dihydrothiophenylmethyl radicals. This ring closure was in competition with dissociation to but-3-enyl radicals and an isothiocyanate. The dissociation predominated at temperatures above ca. 300 K.

AB - But-3-enylthiolmidoyl radicals were shown by EPR spectroscopy and end product analysis to ring-close predominantly in the 5-exo mode with a rate constant of 2.4 x 10(4) s(-1) at 300 K to afford substituted dihydrothiophenylmethyl radicals. This ring closure was in competition with dissociation to but-3-enyl radicals and an isothiocyanate. The dissociation predominated at temperatures above ca. 300 K.

KW - ENANTIOSELECTIVE TOTAL SYNTHESIS

KW - ELECTRON-SPIN RESONANCE

KW - (-)-ALPHA-KAINIC ACID

KW - ARYL ISOTHIOCYANATES

KW - ARYLIMIDOYL RADICALS

KW - AROMATIC ANNELATION

KW - RATE CONSTANTS

KW - ISONITRILES

KW - QUINOLINES

KW - CHEMISTRY

UR - http://www.scopus.com/inward/record.url?scp=0141516243&partnerID=8YFLogxK

U2 - 10.1021/ol034073+

DO - 10.1021/ol034073+

M3 - Other contribution

VL - 5

ER -

Alkenylthioimidoyl radicals: competition between Β-scission and cyclization to dihydrothiophen-2-ylidene-amines

Abstract

Keywords

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