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Croatica Chemica Acta, Vol. 37 No. 1, 1965.

Original scientific paper

1,3-Hydrogen Migration in the Solvolysis of 2-(L'.1 3-Cyclopentenyl)ethyl p-Toluenesulfonate

K. Humski ; Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia
S. Borčić ; Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia
D. E. Sunko ; Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia

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Abstract

2-(Ll 3-Cyclopentenyl)ethyl-1,1-d2 tosylate was prepared and
solvolyzed in 80 per cent aqueous acetic acid. Conversion of the
so1volysis products to exo-2-norbornanol and integration o-f the peak
areas of its n.m.r. spectrum indicates 10-15 per cent of 1,3-deuterium
migration. The hypothesis is advanced that this migration
must have taken place after the rate determining step of the solvolysis.
exo-2-Norbornanol-d2 resulting from this reaction was converted
to the corresponding p-bromobenzenesulfonate and solvolyzed
in acetic acid. Possible explanations for the observed
secondary isotope effect (kH/kD 1.13) are given.

Keywords

Hrčak ID:

208226

URI

https://hrcak.srce.hr/208226

Publication date:

15.5.1965.

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