Letter | Published:

Carbonium Ion Mechanism and Results of Solvolysis of (+)-2-Bromo-octane

Nature volume 204, page 876 (28 November 1964) | Download Citation

Subjects

Abstract

THE remarkable prevalence of re-arrangement in simple alkyl groups during the formation of alkyl halides, and the concomitant loss in optical purity have been loosely ascribed to the intermediate formation of a carbonium cation1. The conversion of an alkyl halide into the alcohol, ester, or ether must therefore be scrutinized for points of correlation. There are few published examples of alkyl rearrangement in the solvolysis of straight chain alkyl halides. Isopropanol was formed in the mercury catalysed solvolysis of n-propyl bromide in aqueous formic acid, and the carbonium ion mechanism was postulated2.

Access optionsAccess options

Rent or Buy article

Get time limited or full article access on ReadCube.

from$8.99

All prices are NET prices.

References

  1. 1.

    , and , J. Chem. Soc., 2310 (1964). , , and , ibid., 2314 (1964).

  2. 2.

    , and , J. Chem. Soc., 4940 (1960).

  3. 3.

    , and , J. Chem. Soc., 1192 (1937).

  4. 4.

    , , and , J. Chem. Soc., 1196 (1937).

  5. 5.

    , , and , J. Chem. Soc., 3480 (1964).

Download references

Author information

Affiliations

  1. Northern Polytechnic, Holloway Road, London, N.7.

    • W. GERRARD
    •  & H. R. HUDSON

Authors

  1. Search for W. GERRARD in:

  2. Search for H. R. HUDSON in:

About this article

Publication history

Published

DOI

https://doi.org/10.1038/204876a0

Further reading

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.