Helvetica Chimica Acta p. 2481 - 2488 (1983)
Update date:2022-08-16
Topics:
Grob, Cyril A.
Waldner, Adrian
The solvolysis rates and products of the tertiary 2-methyl-2-exo- and -2-endo-norbornyl 2,4-dinitrophenyl ethers; 1 and 2, (X=2,4-(NO2)2C6H3O) have been determined.The different sensitivities of the rates of these ethers to the inductive effect of substituents at C(6) indicate that graded bridging of C(2) by C(6) occurs in the ionization of the exo-ethers 1, not, however, in the ionization of the endo ethers 2.In both cases hydrolysis leads to 2-methyl-2-exo-norbornanols only.Consequently, substitution takes place with retention at C(2) in the exo-series 1 and with inversion at C(2) in the endo-series 2.It is concluded that stereoelectronic and polar effects, rather than steric bulk effets, determine the high exo/endo rate ratios of the parent norbornyl derivatives 1a and 2a.
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