59336-73-1Relevant articles and documents
An unprecedented stereoselective base-induced trimerization of an α-bromovinylsulfone
Fisher, Brendan,Lepage, Romain J.,White, Jonathan M.,Ye, Young,Krenske, Elizabeth H.,Rizzacasa, Mark A.
, p. 5529 - 5534 (2017/07/12)
A unprecedented base-induced trimerization of bromovinylsulfone 1 afforded the cyclohexene 6 as a single diastereoisomer. Optimization of this reaction gave the adduct 6 in 49% yield. A mechanistic rationale for the trimerization involving consecutive SN2′ additions and [3,3]-rearrangements and a final stereoselective intramolecular conjugate addition is proposed and supported by M06-2X density functional theory calculations.
Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 12. Extrusion of Ph3P from sulfonyl ylides and reactivity of the resulting sulfonyl carbenes
Aitken, R. Alan,Drysdale, Martin J.,Ferguson, George,Lough, Alan J.
, p. 875 - 880 (2007/10/03)
Twelve sulfonyl stabilised phosphorus ylides have been prepared and their behaviour upon flash vacuum pyrolysis at 600°C has been examined. Examples with an arylsulfonyl substituent undergo loss of Ph3PO to give intractable products but those with an arylmethylsulfonyl substituent separately lose Ph3P and SO2 to give products consistent with the intermediacy of sulfonyl carbenes. X-Ray structure determinations of one ylide from each series show a more significant P-O non-bonding interaction in the first case, providing some explanation for the different thermal reactivity.