Chiral Benzylic Carbocations: Low-Temperature NMR Studies and Theoretical Calculations

D Stadler, A Goeppert, G Rasul, GA Olah…

文献索引：Stadler, Daniel; Goeppert, Alain; Rasul, Golam; Olah, George A.; Prakash, G. K. Surya; Bach, Thorsten Journal of Organic Chemistry, 2009 , vol. 74, # 1 p. 312 - 318

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被引用次数: 35

摘要

The α-chiral secondary and tertiary benzylic carbocations 19− 30 were generated from the corresponding benzylic alcohols 1, 2, and 5− 14 by treatment with FSO3H or FSO3H/SbF5 in SO2ClF as the solvent at− 70° C and characterized by one-and two-dimensional NMR spectroscopy. Coupling constants and NOESY measurements suggest a preferred conformation in which the α-hydrogen atom occupies the 1, 3-allylic-strain position and ...