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Diphenyl sulfide 8 had the following properties: infrared (KBr) 3010 (w), 1590 (m), 1520 (s), 1450 (w), 1325 (s), 1340 (m), 1310 (w), 1260 (w), 1100 (w), 1055 (w), 1040 (w), 915 (w), 880 (w), 810 (w), 790 (m), 750 (w), 735 (s), and 680 cm-1 (w); nmr (CDCls) 5 6,9 (m, 1 H), 7.3 (m, 2 H), 7.8 (m, 2 H), and 8.4 (m, 3H).2,3'-Diaminodiphenyl Sulfide (7).-Hydrogenation of sulfide 8, prepared above (0.20 g, 0.000725 mol) in 100 ml of absolute ethanol at 40 psi over 200 mg of 10% palladium on charcoal for 6 hr, yielded an oil which was distilled at 110°( 0.1 mm). The resulting clear oil, 0.102 g (65%), failed to crystallize. An analytical sample of 7 was obtained by preparative glc.

Sodium cyanoborohydride in hexamethylphos-accommodated by an S,2 process involving direct attack phoramide provides a rapid, convenient and exceedingly by hydride or cyanoborohydride anion. The following selective system for the reductive removal of iodobromo-, tosyloxy-and, indirectly, hydroxy-groups.

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Bei der Reduktion der Tosylhydrazone aliphatischer Aldehyde oder Ketone des Typs (I) bzw. (III) mit Na‐trihydridocyanoborat in einem sauren 1:1‐ Gemisch aus DMF und Sulfolan entstehen ausschließlich die entsprechenden Kohlenwasserstoffe (II) bzw. Cyanester (IV).