Y. Kikuchi, Y. Kato, Yasutaka Tanaka
Feb 1, 1991
Citations
0
Influential Citations
69
Citations
Journal
Journal of the American Chemical Society
Abstract
Resorsinol-dodecanal cyclotetramer 1 in CDCl 3 forms hydrogen-bonded, 1/1 complexes with cyclohexanediols as well as with 2,4-pentane- and 2,5-hexanediol as their open-chain analogues and cyclohexanol and cis- and trans-4-tert-butylcyclohexanol. The affinities to 1 of cyclic diols are significantly larger than those of open-chain diols and monools. Those of regio- and stereoisomers of cyclohexanediol depend on the configuration (axial-equatorial>diequatorial) and relative positions (1,4>>1,2>1,3) of the two OH groups involved and decrease in the order cis-1,4>cis-1,2>trans-1,3>trans-1,4>cis-1,3>trans-1,2; the stereoselectivities are thus cis-1,4/trans-1,4=8.0, cis-1,2/trans-1,2=2.5, and trans-1,3/cis-1,3=1.5. The selectivities in the diol binding are discussed in terms of multiple hydrogen bonding of diol and 1