Chair-boat equilibria in fused cyclohexane systems

✍ Scribed by M. Svoboda; M. Tichý; J. Fajkoš; J. Sicher

• Book ID: 104212586
• Publisher: Elsevier Science
• Year: 1962
• Tongue: French
• Weight: 291 KB
• Volume: 3
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)70939-7

✦ Synopsis

THE energy difference between a chair and a boat form in cyclohexanonel is only about larger, being cyclohexanone few authentic 1 kcal/mole; for cyclohexane2 this difference is very much in the order of 5 kcal/mole. Accordingly boat forms in derivatives are of very wide occurrence3 whereas only very cases are known of boats in cyclohexane derivatives. 4 In this note we report several examples of boat forms in fused cyclohexane systems as well as some semi-quantitative data on the chair-boat equilibria.

The compounds employed in this study are the five aminoalcohols Ia-Va and the five corresponding N,N-dimethyl derivatives Ib-Vb (cf. Fig. 2).

The aminoalcohols were obtained from the appropriate epoxides 5,6 by reaction with ethanolic asnsonia at 180'. The dimethylaminoalcohols were analogously 1 2