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Conformation of Isobutyl, 2,2‐Dibromoethyl, and 2‐Methoxypropyl Side Chains on Cyclohexane and Tetrahydropyran Ring Systems
Author(s) -
Hoffmann Reinhard W.,
Kahrs B. Colin,
Reiß Philipp,
Trieselmann Thomas,
Stiasny HansChristian,
Massa Werner
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200105)2001:10<1857::aid-ejoc1857>3.0.co;2-4
Subject(s) - tetrahydropyran , chemistry , cyclohexane , side chain , ring (chemistry) , stereochemistry , cyclohexane conformation , dimethoxyethane , lithium (medication) , organic chemistry , molecule , polymer , medicine , hydrogen bond , electrode , electrolyte , endocrinology
An isobutyl group placed equatorially in the 2‐position of a 1‐equatorially substituted cyclohexane adopts a preferred conformation (cf. 5 ). This also holds when it is placed in the 2‐position on a 3‐equatorially substituted tetrahydropyran (cf. 6 ). The same conformational preference is found for 2‐methoxypropyl residues in the 2‐position of 3‐substituted tetrahydropyrans (cf. 8 and 10 ). The latter compounds chelate lithium cations as analogues of 1,2‐dimethoxyethane. Through this complexation, it is possible to effect a change in the side chain conformation.