Activation of nitriles by hydrogen bonding in cycloadditions with nitrile oxides

A Corsaro, U Chiacchio, P Caramella…

Index: Corsaro, Antonino; Chiacchio, Ugo; Caramella, Pierluigi; Purrello, Giovanni Journal of Heterocyclic Chemistry, 1984 , vol. 21, p. 949 - 952

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Citation Number: 13

Abstract

950 A. Corsaro, U. Chiacchio, Р. Caramella and G. Purrello Vol.21 [8] undergo preferential syn additions, which maximize hydrogen bonding effects. To test the hydrogen bonding hypothesis we have stud- ied the cycloadditions of benzonitrile oxide to the ortho- aminobenzonitriles 9a-e. These dipolarophiles seemed very convenient models to us. They retain the same geo- metrical features of the prevailing (Z) stereo isomer 6 of /3-aminocinnamonitriles, ie ...

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benzonitrile oxide Structure

873-67-6

benzonitrile oxide

4-CYANOACETANILIDE Structure

35704-19-9

4-CYANOACETANILIDE

~5%

2-oxido-3,4-diphenyl-1-oxa-5-aza-2-azoniacyclopenta-2,4-diene Structure

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N-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl]acetamide Structure

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benzonitrile oxide Structure

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benzonitrile oxide

4-CYANOACETANILIDE Structure

35704-19-9

4-CYANOACETANILIDE

~2%

N-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl]acetamide Structure

93245-20-6

N-[4-(3-phenyl-...

benzonitrile oxide Structure

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benzonitrile oxide

p-Tolunitrile Structure

104-85-8

p-Tolunitrile

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5-(4-methylphenyl)-3-phenyl-1,2,4-oxadiazole Structure

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5-(4-methylphen...

benzonitrile oxide Structure

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benzonitrile oxide

N-(2-Cyanophenyl)benzamide Structure

40288-69-5

N-(2-Cyanopheny...

~0%

2-oxido-3,4-diphenyl-1-oxa-5-aza-2-azoniacyclopenta-2,4-diene Structure

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2-oxido-3,4-dip...

N/A Structure

93245-17-1

N/A

benzonitrile oxide Structure

873-67-6

benzonitrile oxide

Acetamide,N-(2-cyanophenyl)- Structure

25116-00-1

Acetamide,N-(2-...

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N/A Structure

40077-68-7

N/A

2-oxido-3,4-diphenyl-1-oxa-5-aza-2-azoniacyclopenta-2,4-diene Structure

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2-oxido-3,4-dip...

benzonitrile oxide Structure

873-67-6

benzonitrile oxide

4-CYANOACETANILIDE Structure

35704-19-9

4-CYANOACETANILIDE

~0%

2-oxido-3,4-diphenyl-1-oxa-5-aza-2-azoniacyclopenta-2,4-diene Structure

5585-14-8

2-oxido-3,4-dip...

N-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl]acetamide Structure

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N-[4-(3-phenyl-...

benzonitrile oxide Structure

873-67-6

benzonitrile oxide

aminobenzonitrile Structure

1885-29-6

aminobenzonitrile

~0%

2-oxido-3,4-diphenyl-1-oxa-5-aza-2-azoniacyclopenta-2,4-diene Structure

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[2-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl]amine Structure

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aminobenzonitrile Structure

1885-29-6

aminobenzonitrile

~%

2-oxido-3,4-diphenyl-1-oxa-5-aza-2-azoniacyclopenta-2,4-diene Structure

5585-14-8

2-oxido-3,4-dip...

benzonitrile oxide Structure

873-67-6

benzonitrile oxide

N/A Structure

93245-16-0

N/A

~0%

2-oxido-3,4-diphenyl-1-oxa-5-aza-2-azoniacyclopenta-2,4-diene Structure

5585-14-8

2-oxido-3,4-dip...

N/A Structure

93245-19-3

N/A

N/A Structure

40077-68-7

N/A

~87%

[2-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl]amine Structure

40077-67-6

[2-(3-phenyl-1,...

benzonitrile oxide Structure

873-67-6

benzonitrile oxide

aminobenzonitrile Structure

1885-29-6

aminobenzonitrile

~10%

2-oxido-3,4-diphenyl-1-oxa-5-aza-2-azoniacyclopenta-2,4-diene Structure

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2-oxido-3,4-dip...

[2-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl]amine Structure

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[2-(3-phenyl-1,...


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