H. Makomo et al., REDUCTIONS OF PHOSPHONODITHIOFORMATES - SYNTHESES OF ALPHA-PHOSPHONYLTHIOLS AND HEMIDITHIOACETALS, Tetrahedron, 50(34), 1994, pp. 10277-10288
The phosphonodithioformates appeared versatile precursors to the (merc
aptomethyl)phosphonates and derivatives, through sodium borohydride re
duction in acetonitrile heated under reflux. By contrast, when the red
uction was performed at room temperature with sodium borohydride, the
(mercapto-alkylthio-methyl)phosphonates were exclusively obtained; red
uction with BH3-Me(2)S (BMS) or within lithium diisopropylaminoborohyd
ride also led to these hemidithioacetals. The aforementioned products
of reduction were characterized by the syntheses of various derivative
s. In particular, S-phosphonyl trithiocarbonates, N-phenyl imidodithio
carbonate and dithiocarbamate were prepared.