Thermolysis of 7-isopropylidene-2,3-diazabicyclo [2.2.1] hept-2-ene in the presence of spin trap

Jimmy S. Hwang; Mohammad Nahid Siddiqui; Ahmed M. Bukhari

doi:10.1016/S0040-4039(00)79775-9

Thermolysis of 7-isopropylidene-2,3-diazabicyclo [2.2.1] hept-2-ene in the presence of spin trap

Jimmy S. Hwang
, Mohammad Nahid Siddiqui
, Ahmed M. Bukhari^*

^*Corresponding author for this work

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

1 Scopus citations

Abstract

Thermolysis of 7-isopropylidene-2,3-diazabicyclo-[2.2.1] hept-2-ene (1) in the presence of trapping agent, α-phenyl tert-butyl nitrone (2) in acetonitrile solution at 70-90°C produced a six-line EPR spectrum with the following hyperfine coupling constants: AN = 14.9 G and A_H = 2.0 G. The structure was assigned to an isopropylidenecyclopentanyl radical diadduct (5) whose hyperfine coupling constants were found to be consistent with those in cyclohexadienyl adducts (4) observed by Mao and Kevan. The formation of the biradical (3) is ruled out.

Original language	English
Pages (from-to)	3711-3714
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	30
DOIs	https://doi.org/10.1016/S0040-4039(00)79775-9
State	Published - 22 Jul 1991

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Thermolysis of 7-isopropylidene-2,3-diazabicyclo [2.2.1] hept-2-ene in the presence of spin trap",

abstract = "Thermolysis of 7-isopropylidene-2,3-diazabicyclo-[2.2.1] hept-2-ene (1) in the presence of trapping agent, α-phenyl tert-butyl nitrone (2) in acetonitrile solution at 70-90°C produced a six-line EPR spectrum with the following hyperfine coupling constants: AN = 14.9 G and AH = 2.0 G. The structure was assigned to an isopropylidenecyclopentanyl radical diadduct (5) whose hyperfine coupling constants were found to be consistent with those in cyclohexadienyl adducts (4) observed by Mao and Kevan. The formation of the biradical (3) is ruled out.",

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year = "1991",

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T1 - Thermolysis of 7-isopropylidene-2,3-diazabicyclo [2.2.1] hept-2-ene in the presence of spin trap

AU - Hwang, Jimmy S.

AU - Siddiqui, Mohammad Nahid

AU - Bukhari, Ahmed M.

PY - 1991/7/22

Y1 - 1991/7/22

N2 - Thermolysis of 7-isopropylidene-2,3-diazabicyclo-[2.2.1] hept-2-ene (1) in the presence of trapping agent, α-phenyl tert-butyl nitrone (2) in acetonitrile solution at 70-90°C produced a six-line EPR spectrum with the following hyperfine coupling constants: AN = 14.9 G and AH = 2.0 G. The structure was assigned to an isopropylidenecyclopentanyl radical diadduct (5) whose hyperfine coupling constants were found to be consistent with those in cyclohexadienyl adducts (4) observed by Mao and Kevan. The formation of the biradical (3) is ruled out.

AB - Thermolysis of 7-isopropylidene-2,3-diazabicyclo-[2.2.1] hept-2-ene (1) in the presence of trapping agent, α-phenyl tert-butyl nitrone (2) in acetonitrile solution at 70-90°C produced a six-line EPR spectrum with the following hyperfine coupling constants: AN = 14.9 G and AH = 2.0 G. The structure was assigned to an isopropylidenecyclopentanyl radical diadduct (5) whose hyperfine coupling constants were found to be consistent with those in cyclohexadienyl adducts (4) observed by Mao and Kevan. The formation of the biradical (3) is ruled out.

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U2 - 10.1016/S0040-4039(00)79775-9

DO - 10.1016/S0040-4039(00)79775-9

M3 - Article

AN - SCOPUS:0025861466

SN - 0040-4039

VL - 32

SP - 3711

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JO - Tetrahedron Letters

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IS - 30

ER -

Thermolysis of 7-isopropylidene-2,3-diazabicyclo [2.2.1] hept-2-ene in the presence of spin trap

Abstract

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