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Hydrohalogenation Reaction of 1,2‐Allenic Sulfoxides with AlX 3 and H 2 O: Efficient Synthesis of 2‐Haloallyl Sulfoxides
Author(s) -
Ma Shengming,
Wei Qi
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200005)2000:10<1939::aid-ejoc1939>3.0.co;2-v
Subject(s) - chemistry , steric effects , benzene , medicinal chemistry , reaction conditions , sulfoxide , organic chemistry , catalysis
Abstract 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 AlCl 3 and H 2 O on this reaction is discussed and the optimized ratio of allenic sulfoxides, AlCl 3 and H 2 O is 1:0.55:1. For the hydroiodination reaction, a combination of excess NaI, AlCl 3 , and H 2 O was used. The reaction is probably mediated by the species formed from the reaction of AlX 3 with H 2 O. 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.