CAS: 582307-06-0; 3,5-Difluorobenzimidamide

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(3,5-difluorophenyl)diazirine sodium thiophenolate

📜(3,5-Difluorophenyl)Diazirine,Sodium Thiophenolate 以 甲醇 作为反应溶剂,化学反应生成 3,5-二氟苯甲腈,3,5-二氟苯甲脒,二苯二硫醚
参考文献:Reaction Of Arylhalodiazirines With Thiophenoxide: A Redox Process
标题:Reaction Of Arylhalodiazirines With Thiophenoxide: A Redox Process
摘要:Phenylbromodiazirine Reacts With Thiophenoxide Ion In Methanol To Give Benzonitrile,Benzamidine,Ammonia,And Diphenyl Disulfide. The Reaction Is General For Arylhalodiazirines,With Electron-Withdrawing Groups On The Aromatic Ring Exerting A Small Rate-Enhancing Effect. Three Potential Mechanisms Are Suggested For This Redox Process. These Mechanisms Include An N-Sulfenylated Diazirine,A Diazirinyl Radical,And A Diazirinyl Anion. Ring Opening Of These Intermediates And Subsequent Transformations Would Lead To Benzonitriles,Benzamidine,And Ammonia. A Key Intermediate In These Transformations Is Phsnh2,32. This Intermediate Has Been Independently Generated And Found To Rapidly Convert To Ammonia And Diphenyl Disulfide Under The Reaction Conditions. Another Proposed Intermediate,N-(Phenylthio)Benzamidine,38,Has Also Been Independently Generated And Subjected To The Reaction Conditions,Where Benzamidine And More Diphenyl Disulfide Result. Theoretical Calculations Suggest The Existence Of Isomeric Diazirinyl Anions. In Addition To A Diazirinyl Ion With Charge Essentially On Carbon,There Is Also An Allylic-Type Ion With Charge On The Two Nitrogen Atoms. Single-Electron Reduction Of A Diazirinyl Radical Necessarily Leads To A Nitrogen-Centered Diazirinyl Anion. Conversion Of This Anion To The Carbon-Centered Diazirinyl Anion Is A Forbidden Process. These Theoretical Studies Suggest That The Diazirinyl Anion May Be A Viable Intermediate In Solution.
DOI:10.1021/ja00070A003