e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

The Journal of Organic Chemistry

Hydrogen cyanide chemistry. 9. Cycloaddition reactions and nitrenium ion type reactivity of diiminosuccinonitrile

T Fukunaga, RW Begland

Index: Fukunaga, Tadamichi; Begland, Robert W. Journal of Organic Chemistry, 1984 , vol. 49, p. 813 - 821

Full Text: HTML

Citation Number: 9

Abstract

Cycloaddition reactions of diiminosuccinonitrile (DISN) with nucleophilic olefins yield a variety of products including [4+ 21 cycloadducts and aziridines. All of the products derived from l, &dienes, styrene, para-substituted styrenes, cycloheptatriene, norbornene, and norbornadiene can be accounted for by rearrangements of a common intermediate, zwitterionic aziridinium ion. We introduce the concept of reverse polarization and propose ...

4-Fluorostyrene Structure

4-Fluorostyrene

ethanedicarbonimidoyl dicyanide Structure

ethanedicarboni...

~76%

2-amino-3-[2-(4-fluorophenyl)aziridin-1-yl]but-2-enedinitrile Structure

2-amino-3-[2-(4...

5-(2-furyl)-1,4,5,6-tetrahydropyrazine-2,3-dicarbonitrile Structure

5-(2-furyl)-1,4...

~%

5-(furan-2-yl)pyrazine-2,3-dicarbonitrile Structure

5-(furan-2-yl)p...

2-Ethenylfuran Structure

~%

5-(furan-2-yl)pyrazine-2,3-dicarbonitrile Structure

5-(furan-2-yl)p...

5-(4-methoxy-phenyl)-1,4,5,6-tetrahydro-pyrazine-2,3-dicarbonitrile Structure

5-(4-methoxy-ph...

~44%

5-(4-methoxyphenyl)pyrazine-2,3-dicarbonitrile Structure

5-(4-methoxyphe...

2-amino-3-[2-(4-methoxyphenyl)aziridin-1-yl]but-2-enedinitrile Structure

2-amino-3-[2-(4...

~%

5-(4-methoxyphenyl)pyrazine-2,3-dicarbonitrile Structure

5-(4-methoxyphe...

4-Methoxystyrene Structure

4-Methoxystyrene

ethanedicarbonimidoyl dicyanide Structure

ethanedicarboni...

~17%

N/A Structure

5-(4-methoxyphenyl)pyrazine-2,3-dicarbonitrile Structure

5-(4-methoxyphe...

Detail

4-Methylstyrene Structure

4-Methylstyrene

ethanedicarbonimidoyl dicyanide Structure

ethanedicarboni...

~1%

2-amino-3-[2-(4-methylphenyl)aziridin-1-yl]but-2-enedinitrile Structure

2-amino-3-[2-(4...

5-(4-methylphenyl)pyrazine-2,3-dicarbonitrile Structure

5-(4-methylphen...

2-p-Tolyl-1-propene Structure

2-p-Tolyl-1-propene

ethanedicarbonimidoyl dicyanide Structure

ethanedicarboni...

~0%

5-(4-methylphenyl)pyrazine-2,3-dicarbonitrile Structure

5-(4-methylphen...

5-Methyl-5-p-tolyl-1,4,5,6-tetrahydro-pyrazine-2,3-dicarbonitrile Structure

5-Methyl-5-p-to...

4-Methylstyrene Structure

4-Methylstyrene

ethanedicarbonimidoyl dicyanide Structure

ethanedicarboni...

~63%

2-amino-3-[2-(4-methylphenyl)aziridin-1-yl]but-2-enedinitrile Structure

2-amino-3-[2-(4...

5-(4-methylphenyl)pyrazine-2,3-dicarbonitrile Structure

5-(4-methylphen...

N-(4-Methoxybenzyl)-diaminomaleonitril Structure

N-(4-Methoxyben...

~%

5-(4-methoxyphenyl)pyrazine-2,3-dicarbonitrile Structure

5-(4-methoxyphe...

(5S,6S)-5-(4-methoxyphenyl)-6-methyl-1,4,5,6-tetrahydropyrazine-2,3-dicarbonitrile Structure

(5S,6S)-5-(4-me...

~%

5-(4-methoxyphenyl)-6-methylpyrazine-2,3-dicarbonitrile Structure

5-(4-methoxyphe...

trans-Anethole Structure

~%

5-(4-methoxyphenyl)-6-methylpyrazine-2,3-dicarbonitrile Structure

5-(4-methoxyphe...

diazomethane Structure

N-(4-Methoxybenzyl)-diaminomaleonitril Structure

N-(4-Methoxyben...

~24%

2-amino-3-[2-(4-methoxyphenyl)aziridin-1-yl]but-2-enedinitrile Structure

2-amino-3-[2-(4...

ethanedicarbonimidoyl dicyanide Structure

ethanedicarboni...

Norbornadiene Structure

~9%

2,3-Dicyanopyrazine Structure

2,3-Dicyanopyrazine

2-Butenedinitrile, 2-amino-3-(3-azatricyclo[3.2.1.02,4]oct-6-en-3-yl) Structure

2-Butenedinitri...

Detail

ethanedicarbonimidoyl dicyanide Structure

ethanedicarboni...

Norbornadiene Structure

~10%

2,3-Dicyanopyrazine Structure

2,3-Dicyanopyrazine

N/A Structure

Detail

ethanedicarbonimidoyl dicyanide Structure

ethanedicarboni...

1-Propyn-1-amine,N,N-diethyl- Structure

1-Propyn-1-amin...

~62%

5-(diethylamino)-6-methylpyrazine-2,3-dicarbonitrile Structure

5-(diethylamino...

ethanedicarbonimidoyl dicyanide Structure

ethanedicarboni...

cyclohexa-1,3-diene Structure

cyclohexa-1,3-diene

~79%

1,4,4a,5,6,8a-hexahydroquinoxaline-2,3-dicarbonitrile Structure

1,4,4a,5,6,8a-h...

ethanedicarbonimidoyl dicyanide Structure

ethanedicarboni...

2-(diethylamino)-1-phenylacetylene Structure

2-(diethylamino...

~48%

5-(diethylamino)-6-phenylpyrazine-2,3-dicarbonitrile Structure

5-(diethylamino...

phenylene-ethylene Structure

phenylene-ethylene

ethanedicarbonimidoyl dicyanide Structure

ethanedicarboni...

~59%

2-amino-3-(2-phenylaziridin-1-yl)but-2-enedinitrile Structure

2-amino-3-(2-ph...

4-Chlorostyrene Structure

4-Chlorostyrene

ethanedicarbonimidoyl dicyanide Structure

ethanedicarboni...

~51%

2-amino-3-[2-(4-chlorophenyl)aziridin-1-yl]but-2-enedinitrile Structure

2-amino-3-[2-(4...