S. Lin, Wen‐Chung Lin, Yuen-han Yeh
Feb 1, 2000
Citations
0
Influential Citations
0
Citations
Journal
Journal of The Chinese Chemical Society
Abstract
A series of 2-aryl-2-hydroxy-1,1,3,3-tetramethyl-5,8-dioxaspiro[3.4]octanes (1), 3-aryl-3-hydyoxyl-2,2,4,4-tetyramethylcyclobutanones (2), and l-aryl-2,2,4-trimethyl-1,3-pentadiones (3) were studied using 13C NMR analyses. The chemical shifts of C-c are dependent on the substituent groups on the phenyl ring for compounds 1 (ρ =-0.966, R2 = 0.987) and 2 (ρ = −1.378, R2 = 0.998). The chemical shifts of C-a follow a similar trend (ρ =−0.926, R2 = 0.989). In the case of compounds 3, C-c yielded the opposite trend with very poor correlation coefficiency (ρ = 1.22, R2 = 0.179). This result reveals the field effect of a polar bond and resonance-induced changes in pi electron-density at C-1 on the cyclobutanering series.