Alkanethiolation process

Details Alkanethiolation process Alkanethiolation process

1997-05-01

1999-05-11

Raymond, Richard

Organic compounds -- part of the class 532-570 series

Organic compounds

Sulfur containing

C07C319/14

Patent

active

059029064

ABSTRACT:
A mixture formed from one or more alkyl disulfides, benzene, and at least about 1.5 equivalents of Lewis acid catalyst is heated to form alkanethiobenzene. Reaction in a mixture formed from excess benzene, dimethyldisulfide (DMDS) and AlCl.sub.3 in which the mole ratio of AlCl.sub.3 to DMDS was 2:1 was complete in 2 hours and afforded 98% conversion and 93% yield of thioanisole. In contrast, the same reaction when attempted using a 1:1 mole ratio of AlCl.sub.3 to DMDS after 6 hours achieved only 66% conversion and a thioanisole yield of only 35%. So far as is known, this is the first example of a highly efficient electrophilic aromatic substitution of the inactivated benzene ring by an alkanethio group.

REFERENCES:
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Database Chemabs Abstract of Russian journal article, Yushko, et al., "Formation of aryl alkyl and diaryl sulfides under alkylation conditions", Vopr. Khim, Khim Tekhnol., 1994, vol. 32, pp. 18-22.
Abstract of JP 08 245 558, 1996.
Abstract of JP 49 054 338, 1974.
Ranken et al., J. Org. Chem., 1989, 54(12), pp. 2985-2988, Dec. 1989.
Mukaiyama et al., Chemistry Letters, 1993, 1, pp. 1-4, Jan. 1993.
Matsumoto et al., J. Chem. Research, 1995, 1, 34-35, Jan. 1995.

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