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Hydrohalogenation Reaction of 1,2-Allenic Sulfoxides with AlX3 and H2O: Efficient Synthesis of 2-Haloallyl Sulfoxides

✍ Scribed by Shengming Ma; Qi Wei

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 280 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(200005)2000:10<1939::aid-ejoc1939>3.0.co;2-v

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✦ Synopsis

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

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