TY - JOUR
T1 - The trans, anti, trans- and trans, syn, trans-isomers of dicyclohexyl-18- crown-6 and their complexes
AU - Burden, Ian J.
AU - Coxon, Andrew C.
AU - Stoddart, J. Fraser
AU - Wheatley, Colin M.
PY - 1977
Y1 - 1977
N2 - The stereospecific synthesis of the trans, an?i,?rans- (2a) and ?rans, syn, trans- (2b) isomers of dicyclohexyl-18-crown- 6 (2) from the diastereoisomeric (±) - (6a) and meso- (6b) 2,2'-methylenedioxydicyclohexanols has been achieved. A one-step synthesis of the di-trans-isomers (2a and b) from (±) -cyclohexane-rrans-l,2-diol (3) is accompanied by the formation of some ?rans-cyclohexyl-9-crown-3 (1 0). trans, syn.trans-Dicyclohexyl-l8-crown-6 (2b) forms crystalline complexes with alkali metal, ammonium, and primary alkylammonium salts. In methanolic solutions, the stability constants for the complexes with sodium, potassium, and caesium chlorides are greater for the cis, syn,- cis- (2c) and cis, syn, cis- (2d) isomers than they are for either of the di-trans-isomers (2a and b). Also, within each pair of isomers, the syn-isomers (2b and d) form stronger complexes than the anti-isomers (2a and c). All four isomers exhibit selectivity for binding potassium ions.
AB - The stereospecific synthesis of the trans, an?i,?rans- (2a) and ?rans, syn, trans- (2b) isomers of dicyclohexyl-18-crown- 6 (2) from the diastereoisomeric (±) - (6a) and meso- (6b) 2,2'-methylenedioxydicyclohexanols has been achieved. A one-step synthesis of the di-trans-isomers (2a and b) from (±) -cyclohexane-rrans-l,2-diol (3) is accompanied by the formation of some ?rans-cyclohexyl-9-crown-3 (1 0). trans, syn.trans-Dicyclohexyl-l8-crown-6 (2b) forms crystalline complexes with alkali metal, ammonium, and primary alkylammonium salts. In methanolic solutions, the stability constants for the complexes with sodium, potassium, and caesium chlorides are greater for the cis, syn,- cis- (2c) and cis, syn, cis- (2d) isomers than they are for either of the di-trans-isomers (2a and b). Also, within each pair of isomers, the syn-isomers (2b and d) form stronger complexes than the anti-isomers (2a and c). All four isomers exhibit selectivity for binding potassium ions.
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U2 - 10.1039/P19770000220
DO - 10.1039/P19770000220
M3 - Article
AN - SCOPUS:37049103237
SN - 0300-922X
SP - 220
EP - 226
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
ER -