A new method for cyclopentanone annulation - American Chemical

Jul 15, 1983 - 1984, 49, 153-157. 153. Table I. Dehalogenation of ufc-Dihaloalkanes to Alkenes (1 mol) with. Sodium Sulfide (2.5 mol) under Phase-Tran...
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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