374632-05-0Relevant articles and documents
Steric and Electronic Effects in the Synthesis and Regioselective Hydrolysis of Unsymmetrical Imides
Shang, Jing,Pourvali, Aysa,Cochrane, James R.,Hutton, Craig A.
, p. 1854 - 1858 (2015/12/26)
The AgI-promoted coupling reaction of thioamides and carboxylic acids is shown to be a useful method for the generation of unsymmetrical imides. The reaction proceeds efficiently with unhindered and electron-rich or neutral coupling partners, but not with hindered thioamides (such as thiopivalamides) or electron deficient thioamides (such as trifluorothioacetamides). Intriguingly, thioformamides are also ineffective coupling partners, despite having minimal steric or electronic influence. Hindered carboxylic acid coupling partners (such as pivalic acid) are tolerated, but electron deficient acids, such as trifluoroacetic acid, are ineffective coupling partners. Furthermore, an interplay of both steric and electronic effects is observed in the subsequent hydrolysis of unsymmetrical imides. Imides with a dimethoxybenzoyl group give high regioselectivity upon hydrolysis, favouring cleavage of the distal acyl group. Imides with a p-nitrobenzoyl or pivaloyl group give reversed selectivity, favouring cleavage of the proximal acyl group.
Selective synthesis of 1,2-benzisothiazol-3-one-1-oxide nitro derivatives
Serebryakov,Kislitsin,Semenov,Zlotin
, p. 1659 - 1664 (2007/10/03)
A new selective synthesis of 1,2-benzisothiazol-3-one-1-oxide nitro derivatives by reaction of 2-benzylthio-4-nitro- and 2-benzylthio-4,6-dinitrobenzamides with gaseous chlorine in wet CH2Cl2 has been developed Reactions of N-unsubstituted 2-benzylthio-4-nitro- and 2-benzylthio-4,6-dinitrobenzamides with gaseous chlorine in 60% AcOH give, instead of the S-oxides, the appropriate 1,2-benzisothiazol-3-one-1,1-dioxide nitro derivatives.
