73683-07-5Relevant academic research and scientific papers
The Mechanism for Interconversion of Stereoisomers in N-(2,3-Dihydro-2-oxobenzoxazol-3-yl)- and N-(1,2-Dihydro-2-oxoquinolin-1-yl)-N-1-methylallylarenesulphenamides
Atkinson, Robert S.,Judkins, Brian D.
, p. 509 - 513 (2007/10/02)
Stereoisomers of the quinolone and benzoxazolinone-substituted sulphenamides (1) and (2) are interconverted by formal rotation around their N-N (chiral) axes.Two alternative pathways which could result in net rotation have been tested.Neither epimerisation at C-1 via a route involving sigmatropic rearrangement nor radical dissociation-recombination have been found to contribute significantly to interconversion of the stereoisomers.The retarded rate of stereoisomer interconversion in the 4-methylbenzoxazolinone-sulphenamide (16) by comparison with (2) suggests that this process in (2) occurs by simple N-N bond rotation and a similar conclusion has been drawn in the case of (1) by comparison with the rate of racemisation of (19).
