REACTIONS OF THIIRANES. X. REGIOSELECTIVITY OF RING-OPENING IN METHYL- AND VINYLTHIIRANES BY PHENOLS
The effects of substituents in the phenol on the regioselectivity of the ring opening of methyl- and vinylthiiranes with phenols in the presence of 3-chloro-1-propene have been studied.Increasing the electron-donating properties of the substituent in the phenol increases the amount of the isomer corresponding to cleavage of the ring in accordance with Krasurskii's rule.The reaction rate was increased considerably when carried out in highly polar aprotic solvents.
Tverdokhlebov, V. P.,Polyakova, N. Yu.,Tselinskii, I. V.
p. 1258 - 1261
(2007/10/02)
REACTIONS OF THIIRANES. IX. SYNTHESIS AND PMR AND MASS SPECTRA OF SUBSTITUTED PHENOXYTHIAHEXENES
The opening of the substituted thiirane ring by phenolates in methanol with 3-chloro-1-propene as electrophile was investigated.The structure of the obtained phenoxythiahexenes was proved by PMR and mass spectrometry, which made it possible to demonstrate the regioselectivity of the reactions of unsymmetrical thiiranes with phenolates.
Vergizova, T. V.,Rodin, A. A.,Frolova, G. M.,Zenkevich, I. G.,V'yunov, K. A.,Ginak, A. I.
p. 1101 - 1104
(2007/10/02)
REACTIONS OF THIIRANES. VIII. MECHANISM OF THE REACTIONS OF THIIRANES WITH PHENOL UNDER THE CONDITIONS OF BASE CATALYSIS
The effect of the substituent on the rate of the opening of substituted thiiranes by phenol was investigated.The direction of opening of the thiirane ring varies, depending on the electronic character of the substituent; for substituents whose electronic effect is transmitted by an induction mechanism the product corresponding to opening of the thiirane ring according to the Krasuskii rule predominates in the reaction mass.For thiiranes with substituents containing a ?-electron system the opening of the three-membered heterocycle takes place with the formation ofanomalous reaction products.The ratio of the reaction paths to the formation of the isomeric oxathiaalkenes was determined.
Vergizova, T. V.,Rodin, A. A.,V'yunov, K. A.,Ginak, A. I.
p. 2023 - 2026
(2007/10/02)
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