The preparation and the base-promoted Smiles rearrangement of phenylfurazans (series a), 3-phenylfuroxan (series b) and 4-phenylfuroxan (series c) bearing 2-hydroxyethylthio ( 1), 2-hydroxyethylsulfonyl ( 2), carbamoylmethylthio ( 3) and carbamoylmethylsulfonyl ( 4) functions at the hetero-ring are described. Under similar conditions compounds of the series a and b gave the expected Smiles rearrangment products with the only exception being the amide derivatives 3 which were hydrolysed to their corresponding acid. The behaviour of the 4-phenylfuroxan series to Smiles rearrangment was quite different. Under conditions close to those adopted for the corresponding 3-phenyl isomers, 1c and 2c decomposed into unidentified polar products. 3c afforded as principal product 3-mercapto 4-phenylfurazan while 4c afforded (Z)-2-hydroxyimino-2-phenylacetonitrile. Possible mechanisms of formation of these products are discussed.

Unsymmetrically substituted furoxans. Part 18. Smiles rearrangement in furoxan systems and in related furazans

BOSCHI, Donatella;SORBA, Giovanni;BERTINARIA, Massimo;FRUTTERO, Roberta;CALVINO, Rosella;GASCO, Alberto
2001

Abstract

The preparation and the base-promoted Smiles rearrangement of phenylfurazans (series a), 3-phenylfuroxan (series b) and 4-phenylfuroxan (series c) bearing 2-hydroxyethylthio ( 1), 2-hydroxyethylsulfonyl ( 2), carbamoylmethylthio ( 3) and carbamoylmethylsulfonyl ( 4) functions at the hetero-ring are described. Under similar conditions compounds of the series a and b gave the expected Smiles rearrangment products with the only exception being the amide derivatives 3 which were hydrolysed to their corresponding acid. The behaviour of the 4-phenylfuroxan series to Smiles rearrangment was quite different. Under conditions close to those adopted for the corresponding 3-phenyl isomers, 1c and 2c decomposed into unidentified polar products. 3c afforded as principal product 3-mercapto 4-phenylfurazan while 4c afforded (Z)-2-hydroxyimino-2-phenylacetonitrile. Possible mechanisms of formation of these products are discussed.
JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. 1
2001
1751
1757
http://www.rsc.org/publishing/journals/article.asp?doi=b104845g
D. BOSCHI; G. SORBA; M. BERTINARIA; R. FRUTTERO; R. CALVINO; A. GASCO
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2318/1760
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