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1H and 13C NMR study of the neomenthyl halides: A very high field proton shift in the iodide

✍ Scribed by Gordon L. Lange; Christine Gottardo

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
244 KB
Volume
28
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Complete analyses o the ^1^H NMR spectra of neomethyl iodide (1), the bromide (2) and the chloride (3) are reported. Of paticular interest is the very high‐field resonance at −0.16 ppm in 1 which is assigned to H‐4. The same poton in the bromide is also found upfield at 0.78 ppm. H‐4 in these neomenthyl derivatives is tertiary and β‐antipeiplanar to the halogen atom. A similar upfield shift has been reported previously for the tertiary proton in trans‐9‐iododecalin. The reasons or these unusual shifts are not readily apparent and the ^13^C NMR spectra of 1 and 2, which are reported here for the first time, provide no additional clues to explain the shifts.

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