The Journal of Organic Chemistry

Synthesis of [H+. cntnd.(1.1. 1)] X-cryptates assisted by intramolecular hydrogen bonding

PL Anelli, F Montanari, S Quici

Index: Anelli, Pier Lucio; Montanari, Fernando; Quici, Silvio Journal of Organic Chemistry, 1985 , vol. 50, # 19 p. 3453 - 3457

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Citation Number: 25

Abstract

Condensation of [1.11 diazacoronand and diethylene glycol bis (methanesu1fonate) as well as with its alkylsubstituted derivatives in the presence of 1 molar equiv of BuLi or KH gives the corresponding [H+ c (lll)] X-cryptates in 3143% yields. Experimental results indicate that in the intermediate monosubstituted diazacoronand, the NH hydrogen plays a templating role, thus favoring the bicyclic ring closure by intramolecular hydrogen bonding. Similar ...