Naslov
The endergonic ene-reaction of alkenes and SO, can now be used to prepare alpha, beta unsaturated sulfones and sulfonamides

Autori
Dean Markovic, A. Varela-Alvarez, J. A. Sordo, P. Vogel

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Chimia / - , 2009, 450-450

Skup
Swiss Chemical Society Meeting

Mjesto i datum
Lausanne, Švicarska, 04.09.2009

Vrsta sudjelovanja
Predavanje

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
SO2, mechanistic studies, ene reaction, sulfinic acid Lewis acid complexes

Sažetak
In our group we develop S02 chemistry for synthesis of polyketides and polypropionates, coupling reactions of sulfonyl chlorides and new neutral silylation agents. 1 We have found polysulfones as organic catalysts for alkene isomerization. Based on our mechanistic work we have developed green, metal free che1noselective deprotection of allylic ethers.2b Here we report studies on the potential energy surfaces of the desulfinylation of allylsulfinic acid by quantum calculations and together with kinetic data obtained for the reaction in absence or presence of additives. For the first time we manage to carry out the ene reaction of unactivated alkenes and 802 . Although it's elemental character and high importance for chemical community, the ene reaction could not be applied because of its endergonicity. We found a way to stabilize the product of the reaction allylsulfinic acids by building tetra1neric complex 2 of the acid with BCl3. These stabilized complexes can be transformed to sulfones, sulfonyl chlorides, sulfona1nides, sulfinic esters and salts in high yields.

Izvorni jezik
Engleski

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