A novel heterocyclic sulfur ylide, 2-t-butyl-3-methyl-1-phenylbenzothiazolinium ylide 13) was generated as an intermediate in the reaction of 2-t-butyl-3-methylbenzothiazolze (2) with benzyne. The S-ylide 13 underwent a novel intermolecular [1,2] shift to give 2-t-butyl-3-methyl-2-phenylbenzothiazom
Sulfur ylides generated from the reaction of adamantylidene and phenylcarbene with sulfur substrates
β Scribed by Yuri N Romashin; Michael T.H Liu; Brian T Hill; Matthew S Platz
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 153 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Reaction of adamantylidene and phenylcarbene with ethylthiol, ethylene dithiol, allylethylsulfide, allylphenylsulfide, and trimethylenesulfide involves the formation of a sulfur ylide intermediate, followed by H-migration, 2,3-sigmatropic shift, or ring opening to give sulfides. The sulfur ylide formed in the reaction of phenylcarbene with trimethylenesulfide is directly observed by laser flash photolytic techniques.
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Reaction of arylchlorodiazirines with trimethylenesulfide gives a mixture of aryldi(3-chloropropyl)thioacetal and aryl(2-propenyl)(3-chloropropyl)thioacetal in a good yield. The reaction goes through a formation of a sulfur ylide as an intermediate. Rate constants have been determined using laser fl
## Abstract Cyclopentanones 1, 4 and 7, as well as uloses 11, 14, 17, and 20, all possessing an oxygen atom in Ξ±βposition with respect to the carbonyl group, have been allowed to react with dimethylsulfonium and dimethyloxosulfonium methylides. It has been found that the nucleophilic attack can be