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Compounds with bridgehead nitrogen. Part 64—conformational equilibria in the 6-p-nitrophenylperhydrodipyrido[1,2-c: 2′,1′-e]imidazoles

✍ Scribed by Lee Banting; Trevor A. Crabb

Publisher: John Wiley and Sons
Year: 1990
Tongue: English
Weight: 358 KB
Volume: 28
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1260281208

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✦ Synopsis

Abstract

The effect of 6‐substitution on the conformational equilibria of the perhydrodipyrido[1,2‐c:2′,1′‐e]imidazoles has been investigated. r‐6H,t‐11a,t‐11b‐6‐p‐Nitrophenylperhydrodipyrido[1,2‐c:2′,1′‐e]imidazole was found to exist as a pair of enantiomeric non‐interconverting N‐outside‐cis‐syn‐trans conformers, whereas the r‐6__H__,c‐11a,c‐11b and r‐6__H,c__‐11a,t‐11b isomers adopted the trans‐syn‐trans conformations. Both syn isomers exhibit restricted rotation of the 6‐p‐nitrophenyl substituent at room temperature and below.

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Compounds with bridgehead nitrogen. 42—1H NMR and stereochemistry of isomeric 6a-methylperhydroindolo[3,2,1-i,j]benzoxazines and the position of conformational equilibrium in perhydropyrrolo[1,2-c][1,3]oxazine

✍ Trevor A. Crabb; Roger F. Newton; Janet Rouse 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 English ⚖ 298 KB

## Abstract The ^1^H NMR parameters of the NCH~2~O protons in the spectrum of perhydropyrrolo[1,2‐__c__][1,3]oxazine show its existence in solution at room temperature in the __O__‐inside __cis__‐fused conformation. __rel__‐(3a__S__,6a__S__,6b__R__,10a__S__,11a__S__)‐6a‐Methylperhydroindolo[3,2,1‐_