R. Beugelmans et al., S(RN)1 SYNTHESIS OF VIC-DINITRO COMPOUNDS CONTAINING A NITRODIOXANE SUBUNIT, Journal of the Chemical Society. Perkin transactions. I, (6), 1995, pp. 609-611
vic-Dinitro compounds containing a nitrodioxane subunit can be obtaine
d by S(RN)1; reactions between either open chain gem-chloronitro deriv
atives as substrates and an anion from nitrodioxane as the nucleophile
or 'reversed' reagents namely gem-chloronitrodioxane (substrate) and
anions from nitro derivatives. The former access is more efficient and
is rationalized on the basis that the structure of the radical anion
generated by mono electron transfer to the respective substrates allow
s an appropriate choice of reagents for optimizing the yield of the ti
tle compounds to be made.