J. Org. Chem. 1984,49, 153-157
153
Table I. Dehalogenation of uic-Dihaloalkanes to Alkenes (1mol) with Sodium Sulfide (2.5 mol) under Phase-Transfer Conditionsa cat., mol
substrate meso-l,2-dibromo-1,2-diphenylethane
0.01 0.02 0.05 0.00 0.01 0.01 0.05 0.01
d,E-1,a-dibromo-1,2-diphenylethane meso-l,2-dichloro-l,2-diphenylethane methyl ery thro-2,3-dibromo-3-phenylpropanoate 0.01 methyl threo-2,3-dibromo-3-phenylpropanoate trans- 1,2-dibromocyclohexane 0.01 0.01 5a ,6p-dibromocholestan-3p-o1
T, "C 25 25 25 25 0 25
time, min(h)
conv,b yield: %
%
products
100 100 100 0.00 100 100 90 100
97
trans-stilbene trans-stilbene trans-stilbene
97
%
%
cis
trans
25
30d 15
