The Search for Persistent Cyclobutylmethyl Cations in Superacidic Media and Observation of the Cyclobutyldicyclopropylmethyl Cation

Author

G. K. Surya Prakash
Prakash Reddy, Missouri University of Science and TechnologyFollow
Golam Rasul
Joseph Casanova
George Andrew Olah

Abstract

Primary and secondary cyclobutylmethyl cations were found to be elusive in superacidic media even at low temperatures. They give thermodynamically more stable rearrangement products, i.e., the dimeric bicyclo[4.4.0]dec-1-yl cation and substituted cyclopentyl cations, respectively. In the search for a persistent cyclobutylmethyl cation, the more stabilized cyclobutyldicyclopropylmethyl cation was prepared from its corresponding alcohol in FSO₃H/SO₂CIF at -90 °C. Using variable-temperature ¹³C NMR studies and theoretical calculations, the ion was shown to exist preferentially in its bisected conformation at -80 °C. The ion is predominantly classical, with expected significant delocalization into the neighboring cycloalkyl rings.

Recommended Citation

G. K. Prakash et al., "The Search for Persistent Cyclobutylmethyl Cations in Superacidic Media and Observation of the Cyclobutyldicyclopropylmethyl Cation," Journal of the American Chemical Society, vol. 120, no. 51, pp. 13362 - 13365, American Chemical Society (ACS), Dec 1998.

The definitive version is available at https://doi.org/10.1021/ja9828962

Department(s)

Chemistry

International Standard Serial Number (ISSN)

0002-7863

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 1998 American Chemical Society (ACS), All rights reserved.

Publication Date

01 Dec 1998