ISSN:
1434-193X
Keywords:
Sulfur
;
Halogens
;
Hydrohalogenation
;
Lewis acids
;
Sulfoxides
;
Sulfoxides
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The hydrohalogenation reaction of 1,2-allenic sulfoxides 1 afforded 2-haloallyl sulfoxides 2 with yields ranging from 56 to 89%. The influence of the ratio of AlCl3 and H2O on this reaction is discussed and the optimized ratio of allenic sulfoxides, AlCl3 and H2O is 1:0.55:1. For the hydroiodination reaction, a combination of excess NaI, AlCl3, and H2O was used. The reaction is probably mediated by the species formed from the reaction of AlX3 with H2O. Because of the steric hindrance of the substrates, the hydrohalogenation of 1-methyl-1-(methylsulfinyl)-1,2-propadiene (1e), (1-methyl-1,2-propadienylsulfinyl)benzene (1f), and (3-methyl-1,2-butadienylsulfinyl)benzene (1g) did not proceed under the same reaction conditions.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
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