Tetrahedron

The role of the hydrogen bonding in cycloadditions of benzonitrile oxide with cyanophenols

A Corsaro, G Buemi, U Chiacchio, G Perrini, V Pistarà…

Index: Corsaro, Antonino; Buemi, Giuseppe; Chiacchio, Ugo; Perrini, Giancarlo; Pistara, Venerando; Romeo, Roberto Tetrahedron, 1996 , vol. 52, # 23 p. 7885 - 7892

Full Text: HTML

Citation Number: 10

Abstract

The reaction of 2 with BNO, generated in situ from the benzhydroximic acid chloride and triethyl amine at 0°C, affords the following products after 24 h at room temperature: the dimerization products of BNO, unreacted 2-cyanophenol, expected 3-phenyl-5-(2-hydroxyphenyl)-1,2,4-oxadiazole (43%), 2-cyanophenyl benzoate (25%) deriving from the unstable O-(2-cyanophenyl) benzohydroxamate and several other products which were not characterized.

Related Articles:

A novel synthesis of 1, 2, 4-oxadiazoles and isoxazoles

[Kivrak, Arif; Zora, Metin Tetrahedron, 2014 , vol. 70, # 4 p. 817 - 831]

A novel synthesis of 1, 2, 4-oxadiazoles and isoxazoles

[Kivrak, Arif; Zora, Metin Tetrahedron, 2014 , vol. 70, # 4 p. 817 - 831]

Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes

[Yoshimura, Akira; Middleton, Kyle R.; Todora, Anthony D.; Kastern, Brent J.; Koski, Steven R.; Maskaev, Andrey V.; Zhdankin, Viktor V. Organic Letters, 2013 , vol. 15, # 15 p. 4010 - 4013]

Orthogonal aerobic conversion of N-benzyl amidoximes to 1, 2, 4-oxadiazoles or quinazolinones

[Zhang, Feng-Lian; Wang, Yi-Feng; Chiba, Shunsuke Organic and Biomolecular Chemistry, 2013 , vol. 11, # 36 p. 6003 - 6007]

Sulfate Radical Anion (SO4•–) Mediated C (sp3)–H Nitrogenation/Oxygenation in N-Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/ …

[Wang, Yi-Feng; Zhang, Feng-Lian; Chiba, Shunsuke Organic Letters, 2013 , vol. 15, # 11 p. 2842 - 2845]

More Articles...