Tetrahedron Letters p. 4859 - 4862 (1983)
Update date:2022-08-03
Topics:
Ohkata, Katsuo
Takee, Kohichi
Akiba, Kin-ya
The rate of methyl transfer to pyridine-d5 of ?-ammoniomethylsulfurane, i.e., S,N-dimethyl-6,7-dihydro-5H-dibenzo<1,5> thiazocinium salt(1), was slower by 1300 times than that of methyldiphenylsulfonium salt (3).Activation parameters at 25 deg C were obtained for 1, ΔH(excit.)=23.1, ΔS(excit.)=-7.8, and for 3, ΔH(excit.)=18.1 kcal/mol, ΔS(exit.)=-10.3 e.u., which are in accord with the hypervalent bonding of 1.
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