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Alkyl Halide |
Nucleophile |
Catalyst (mole equivalent) |
Temperature (°C) |
Time (minutes) |
Yield of Sulfidea(%) |
---|---|---|---|---|---|
Na2Sb |
0.1 |
70 |
40 |
91 |
|
Na2Sb |
0.1 |
70 |
300 |
90 |
|
Na2Sb |
0.1 |
70 |
20 |
91 |
|
Na2Sb |
0.1 |
70 |
80 |
91 |
|
Na2Sb |
0.1 |
70 |
500 |
81c |
|
C2H5SNad |
0.033 |
40 |
40 |
90 |
|
C2H5SNad |
0.033 |
70 |
250 |
88 |
|
C2H5SNad |
0.033 |
40 |
15 |
91 |
|
C2H5SNad |
0.033 |
70 |
120 |
89 |
|
C6H5SNad |
0.033 |
40 |
30 |
92 |
|
C6H5SNad |
0.033 |
70 |
180 |
90 |
|
C6H5SNad |
0.033 |
40 |
10 |
91 |
|
C6H5SNad |
0.033 |
70 |
60 |
90 |
|
aIsolated products. |
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bMole ratio of Na2S to alkyl halide is 0.6. |
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cReaction carried out under nitrogen. |
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dMole ratio of sodium salt to alkyl halide is 1. |
Appendix
Compounds Referenced (Chemical Abstracts Registry Number)
silica
ethanol (64-17-5)
calcium chloride (10043-52-4)
ether, diethyl ether (60-29-7)
sodium hydroxide (1310-73-2)
sodium chloride (7647-14-5)
1-Bromooctane (111-83-1)
nitrogen (7727-37-9)
sodium (13966-32-0)
sodium sulfide (1313-82-2)
Thiophenol, Benzenethiol (108-98-5)
lithium aluminum hydride (16853-85-3)
hexane (110-54-3)
1-bromohexadecane (112-82-3)
boron trifluoride-diethyl etherate (109-63-7)
diphenyl disulfide (882-33-7)
tributylphosphine (998-40-3)
Neopentyl phenyl sulfide, Benzene, [(2,2-dimethylpropyl)thio]- (7210-80-2)
1-bromo-2,2-dimethylpropane, neopentyl bromide, Neopentylbromide (630-17-1)
tributylhexadecylphosphonium bromide (14937-45-2)
tricaprylylmethylammonium chloride (5137-55-3)
1-Chlorooctane (111-85-3)