Die Ableitung der Stereochemie von 1‐Isopropyl‐4‐methyl‐bicyclo[3.1.0]hexan ( cis ‐und  trans ‐Thujan) durch Protonenresonanz‐Spektroskopie | Zendy

Dieffenbacher A. | Zendy; von Philipsborn W. | Zendy

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Die Ableitung der Stereochemie von 1‐Isopropyl‐4‐methyl‐bicyclo[3.1.0]hexan ( cis ‐und trans ‐Thujan) durch Protonenresonanz‐Spektroskopie

Author(s) -

Dieffenbacher A.,

von Philipsborn W.

Publication year - 1966

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19660490212

Subject(s) - chemistry , cyclopentane , ring (chemistry) , stereochemistry , isopropyl , absolute configuration , bicyclic molecule , medicinal chemistry , organic chemistry

100 Mc/s proton NMR. spectra of the two diastereoisomeric thujanes obtained by reduction natural thujone have been measured and are given a detailed analysis. The relative configurations of the two hydrocarbons are deduced. Together with the known R ‐configuration at C(1) the absolute configurations can be derived, (−)‐ cis ‐thujane having the (1 R :4 S :5 R )‐ and (+)‐ trans ‐thujane the (1 R :4 R :5 R )‐configuration. It can be shown that the trans ‐isomer adopts a boat‐like conformation of the bicyclohexane ring system whereas cis ‐thujane prefers a half‐chair conformation with a flattened cyclopentane ring.

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