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BCl3-Mediated H-Ene Reaction of Sulfur Dioxide and Unfunctionalized Alkenes (CROSBI ID 221549)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Markovic, D. ; Volla, C. M. R. ; Varela-Álvarez, A. ; Sordo, J. A. ; Vogel, P. BCl3-Mediated H-Ene Reaction of Sulfur Dioxide and Unfunctionalized Alkenes // Chemistry : a European journal, 20 (2010), 5969-5975. doi: 10.1002/chem.201000164

Podaci o odgovornosti

Markovic, D. ; Volla, C. M. R. ; Varela-Álvarez, A. ; Sordo, J. A. ; Vogel, P.

engleski

BCl3-Mediated H-Ene Reaction of Sulfur Dioxide and Unfunctionalized Alkenes

The first ene reactions of SO(2) and unfunctionalized alkenes are reported. Calculations suggest that the endergonic ene reactions of SO(2) with alkenes can be used to generate beta, gamma-unsaturated sulfinyl and sulfonyl compounds. Indeed, in the presence of one equivalent of BCl(3), the unstable sulfinic acid form stable sulfinic acid.BCl(3) complexes that can be reacted in situ with NCS to generate corresponding sulfonyl chlorides, or with a base to generate corresponding sulfinates. The latter can be reacted with electrophiles to generate sulfones, or with silyl chloride to form beta, gamma-unsaturated silyl sulfinates. The sulfinic acid.BCl(3) complexes can be reacted with ethers that act as oxygen nucleophiles to produce corresponding sulfinic esters. Thus one-pot, three-component synthesis of beta, gamma-unsaturated sulfonamides, sulfinyl esters and sulfones have been developed starting from alkenes and sulfur dioxide (reagent and solvent).

sulfinic acid; ene reaction; computation studies

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Podaci o izdanju

20

2010.

5969-5975

objavljeno

0947-6539

10.1002/chem.201000164

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