Tetrahedron p. 1509 - 1516 (1985)
Update date:2022-07-31
Topics:
Mathur, Naresh C.
Snow, Miles S.
Young, Kent M.
Pincock, James A.
Rate constants for the pyrolysis of 1-diazo-4,4-dimethyl-1,4-dihydronaphtalenes, 4a-4e, have been measured in methanol:6percent triethylamine.In contrast to non-rigid cases, like diphenyldiazomethanes, where all para substituents show a rate increase compared to hydrogen, these rates show a linear Hammett correlation for all para substituents with ?+ = -0.84.This observation is rationalized by a non-linear process for loss of nitrogen leading directly to the ground-state singlet of the carbene, 17.This carbene is then trapped to give ether 11.
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Doi:10.1021/jm00150a004
(1985)Doi:10.1016/S0040-4039(00)98355-2
(1985)Doi:10.1021/jo00223a018
(1985)Doi:10.1002/anie.201808840
(2019)Doi:10.1021/ja0157393
(2001)Doi:10.1039/c39850000498
(1985)
