TY - JOUR
T1 - The [2,3]-sigmatropic rearrangement of propargyl benzenesulphinates to allenyl phenyl sulphones
AU - Braverman, S.
AU - Mechoulam, H.
PY - 1974
Y1 - 1974
N2 - α-Methyl-, α-phenyl-, α,α -dimethyl-, and α-ethyl-α-methylpropargyl benzenesulphinates were found to undergo thermal rearrangement in high yields to sulphones, accompanied by a simultaneous acetylene-allene isomerization. The allenic sulphones produced by the rearrangement of the α-monosubstituted propargyl esters underwent further rearrangement under the reaction conditions, to γ-substituted propargyl phenyl sulphones, by way of a base-catalyzed [1,3] - prototropic shift. A kinetic study of the rearrangement reaction was carried out using two different esters. This study revealed that the rearrangement exhibited a relatively low sensitivity to the effect of solvent ionizing power and substituents. These data and other pertinent evidence suggest a concerted [2,3] - sigmatropic rearrangement.
AB - α-Methyl-, α-phenyl-, α,α -dimethyl-, and α-ethyl-α-methylpropargyl benzenesulphinates were found to undergo thermal rearrangement in high yields to sulphones, accompanied by a simultaneous acetylene-allene isomerization. The allenic sulphones produced by the rearrangement of the α-monosubstituted propargyl esters underwent further rearrangement under the reaction conditions, to γ-substituted propargyl phenyl sulphones, by way of a base-catalyzed [1,3] - prototropic shift. A kinetic study of the rearrangement reaction was carried out using two different esters. This study revealed that the rearrangement exhibited a relatively low sensitivity to the effect of solvent ionizing power and substituents. These data and other pertinent evidence suggest a concerted [2,3] - sigmatropic rearrangement.
UR - http://www.scopus.com/inward/record.url?scp=0001069140&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)97078-4
DO - 10.1016/S0040-4020(01)97078-4
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AN - SCOPUS:0001069140
SN - 0040-4020
VL - 30
SP - 3883
EP - 3890
JO - Tetrahedron
JF - Tetrahedron
IS - 21
ER -