Preparation, ¹³C NMR and IGLO/DFT Studies of Trifluoromethyl Substituted Allyl Cations

Author

G. K. Surya Prakash
Shobha Kantamani
Prakash Reddy, Missouri University of Science and TechnologyFollow
Golam Rasul

Abstract

α-Trifluoromethyl substituted allyl cations 3 and 4 have been prepared by ionizing their corresponding alcohols with SbF₅ in SO₂CIF at low temperatures. The barriers to rotation around the C1-C2 bond of the both cations were determined to be about 9 kcal/mol. The unusually low barriers as compared with their methyl analogues are rationalized by the unsymmetrical nature of the cations. CF₃-substituted cyclohexenyl cations 8 and 10 were also prepared and characterized by ¹³C NMR spectroscopy. Density functional theory (DFT) calculations were performed to investigate geometries and charge densities of tifluoromethyl substituted allyl cations. ¹³C NMR chemical shifts of the cations were also calculated by IGLO method and compared with the experimental results.

Recommended Citation

G. K. Prakash et al., "Preparation, ¹³C NMR and IGLO/DFT Studies of Trifluoromethyl Substituted Allyl Cations," Research on Chemical Intermediates, vol. 22, no. 8, pp. 717 - 724, Springer Verlag, Aug 1996.

The definitive version is available at https://doi.org/10.1163/156856796X00278

Department(s)

Chemistry

International Standard Serial Number (ISSN)

0922-6168

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 1996 Springer Verlag, All rights reserved.

Publication Date

01 Aug 1996