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Carbon-13 NMR Studies. 127—13C and 2H NMR investigations of 1H/2H exchange in isomeric tricyclic [5.2.1.0] and [5.3.1.0] ketones

✍ Scribed by Jeffrey L. Jurlina; Hemant A. Patel; Sriyawathie Peiris; J. B. Stothers

Publisher
John Wiley and Sons
Year
1987
Tongue
English
Weight
584 KB
Volume
25
Category
Article
ISSN
0749-1581

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✦ Synopsis

Under strongly basic conditions (f-BuO-/f-BuOD at 185 "C), the 9,9-dirnethyltricycl0[5.2.1.0~~~]-and -[5.2.1.0'*5]decan-8-ones and the homologous [5.3.1.0]undecanones undergo multi-site 'H/'H exchange. The total 2H uptake was monitored by mass spectrometry, while the individual sites of exchange were established by 13C NMR spectroscopy. The relative rates and stereoselectivity of incorporation at each site were determined by 'H NMR. These results extend our knowledge on the activating effect of the carbonyl group for proton abstraction at remote centres and are compared with earlier data for several related bi-and tricyclic systems. In addition, the 13C spectra provide several examples of geminal 2nd vicinat *H-induced isotope shifts in tricyclic carbon skeletons. KEY WORDS 13C NMR *H NMR Isomeric tricyclic [5.2.1.0] and [5.3.1.0] ketones 'H/'H exchange

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