The Journal of Organic Chemistry

Transmission of polar substituent effects in the adamantane ring system as monitored by 19F NMR: hyperconjugation as a stereoinductive factor

W Adcock, NA Trout

Index: Adcock, William; Trout, Neil A. Journal of Organic Chemistry, 1991 , vol. 56, # 10 p. 3229 - 3238

Full Text: HTML

Citation Number: 43

Abstract

A limited series of (a-and (Z)-bsubstituted adamant-2-yl fluorides 8 and 9, respectively, has been synthesized and characterized, and the'q chemical shifts have been measured in several solvents. A wide range of lSF substituent chemical shifts (SCS, ppm) are obtained for the former system (ca. 9.1 (c-C6HI2), 9.6 (CDC13), and 11.8 (HFIP)) compared to the latter (ca. 0.6 (c-C6H12), 0.7 (CDC13), and 2.3 (HFIP)). Factorization of the'8F SCS into polar ...