REDUCTIVE REMOVAL OF HALOGEN BY THIOLATES FROM 1-HALOCYCLO-PROPYL SULFIDES |
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| Authors: | R Jorritsma H Steinberg Th J de Boer |
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| Institution: | Laboratory for Organic Chemistry , University of Amsterdam , Nieuwe Achtergracht 129, Amsterdam, The Netherlands |
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| Abstract: | Abstract Nucleophilic substitution of cyclopropyl halides or tosylates is often accompanied by ring rupture, but this can be prevented by the presence of an electron releasing substituent in α-position (NR2, OR, SR). Alkylthio and arylthio groups are particularly effective in stabilizing intermediate cyclopropyl cations. These give with most nucleophiles e.g. alkoxide, azide, fluoride, in relatively rapid reactions good yields of substitution products. |
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| Keywords: | Ames assay base-pair mutation mutagenesis phosphoramidothioate thionamide thiophosphoramide |
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