Nitrile Oxide-BF3 complex as electrophilic moiety towards aromatic systems: Stereospecific synthesis of oximes

Auricchio, S.; Bini, Antonella; Pastormerlo, Eros; Ricca, A.; Truscello, Ada

doi:10.1016/s0040-4020(01)90486-7

Cited by 9 publications

(2 citation statements)

References 8 publications

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“…It was dried, and the solvent was removed. Column chromatography gave 4‐(2,6‐dichlorophenyl)‐1,1‐diphenyl‐1 H ‐2,3‐benzoxazine ( 3 , 0.26 g, 20%), ( E )‐2,6‐dichlorobenzophenone oxime ( 4a ,4a 0.32 g, 40%), and 2,6‐dichlorobenzanilide ( 5a , 0.16 g, 20%).…”

Section: Methodsmentioning

confidence: 99%

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Reactions between Nitrile Oxides and Carbenium Ions: Synthesis of Benzoxazines, Oximes, and Amides through Intramolecular ortho or ipso Attack

2002

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Reactions between nitrile oxides and benzylic carbocations are described. Different results were obtained when the carbocations were generated from the corresponding chlorides with different Lewis acids, with addition products such as benzoxazines, oximes, and amides being produced. Primary, secondary, and tertiary carbocations showed different reactivities. The product ratios strongly depended on the substituents on the aromatic ring of the benzylic carbocations. Evidence for the proposed mechanism is reported. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

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Section: Methodsmentioning

confidence: 99%

“…Reaction between 6c and 1: Treatment of 6c (0.50 g, 1.9 mmol) with 1 (0.36 g, 1.9 mmol) in the presence of HBF 4 (0.26 mL) afforded, after workup and purification, ( E )‐2,6‐dichloro‐4′‐methoxybenzophenone oxime ( 4c ,4a 0.33 g, 59%) and 2′,6′‐dichloro‐4‐methoxybenzanilide ( 5c ,4a 0.12 g, 21%).…”

Section: Methodsmentioning

confidence: 99%

Reactions between Nitrile Oxides and Carbenium Ions: Synthesis of Benzoxazines, Oximes, and Amides through Intramolecular ortho or ipso Attack

2002

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Synthesis of Oximes and Hydroxamic Acids

Porcheddu¹,

Giacomelli²

2010

Patai's Chemistry of Functional Groups

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Stereospecific 1,4‐Metallate Shift Enables Stereoconvergent Synthesis of Ketoximes

et al. 2019

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Reported herein is as tereospecific 1,4-metallate rearrangement for single-geometry ketoxime synthesis from oxime chlorides and arylboronic acids.T his strategy exhibits broad substrate scope with excellent stereoselectivity under mild reaction conditions.Incomparison with the conventional approaches,each configuration of unsymmetric diaryl oximes, as well as the thermodynamically less stable Zisomer of aryl alkylk etoximes can be selectively and exclusively obtained. The reactivities of unsymmetric diaryl oximes and the Zisomer of aryl alkylo ximes,aclass of underexplored molecules, enables efficient access to the corresponding isoquinolines, isoquinoline N-oxides,a nd amides having as ingle configuration.

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Nitrile Oxide-BF3 complex as electrophilic moiety towards aromatic systems: Stereospecific synthesis of oximes

Cited by 9 publications

References 8 publications

Reactions between Nitrile Oxides and Carbenium Ions: Synthesis of Benzoxazines, Oximes, and Amides through Intramolecular ortho or ipso Attack

Reactions between Nitrile Oxides and Carbenium Ions: Synthesis of Benzoxazines, Oximes, and Amides through Intramolecular ortho or ipso Attack

Synthesis of Oximes and Hydroxamic Acids

Stereospecific 1,4‐Metallate Shift Enables Stereoconvergent Synthesis of Ketoximes

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