- Magnesium amide-induced pummerer-type reactions of cyclopropyl sulfoxides. Synthesis of cyclopropanone dithioacetals
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The reaction of cyclopropyl phenyl sulfoxide with a magnesium amide, generated from ethylmagnesium bromide and diisopropylamine, gave 1-(phenylthio)cyclopropanol in 72% yield. When the diisopropylmagnesium reagent was treated with a thiol prior to an interaction with cyclopropyl phenyl sulfoxides, symmetrical and unsymmetrical cyclopropanone dithioacetals were produced in fair yields along with small quantities of the corresponding 1-(phenylthio)cyclopropanols.
- Kobayashi, Kazuhiro,Horita, Masatoshi,Irisawa, Susumu,Matsunaga, Akihiro,Morikawa, Osamu,Konishi, Hisatoshi
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p. 1367 - 1369
(2007/10/03)
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- SRN1 Reactions of Halocyclopropanes with Benzenethiolate Ion
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Ultraviolet irradiation of gem-dibromocyclopropanes 1 with benzenethiolate ion in liquid ammonia or in Me2SO solutions gave dithioacetals 2 and, in some cases, cyclopropyl phenyl sulfides 3.The reactions did not proceed in the dark and they were inhibited by m-dinitrobenzene, di-tert-butyl nitroxide, and oxygen.The bromocyclopropane 6a underwent a similar, but slower, reaction.Treatment of the bromochlorocyclopropane 7b led to replacement of only the bromine, while the dichlorocyclopropane 9b was inert under the reaction conditions.The results appear consistent with a radical chain mechanism.
- Meijs, Gordon F.
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p. 606 - 611
(2007/10/02)
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- STRAIN AND SELECTIVITY: PARTNERS FOR ORGANIC SYNTHESIS
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The development of two new small-ring conjunctive reagents, (E)-2-(hydrohymethyl)cyclopropyl phenyl sulphide and 1,1-bis(benzenesulphonyl)cyclopropane, are reported.The former permits a synthesis of 2,4-disubstituted cyclobutanones and (E)-4-phenylthio-4-
- Trost, Barry M.
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p. 139 - 150
(2007/10/02)
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