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The conformational preference of some 4-thia-1-aza-bicyclo[4.1.0]Hept-2-enes

✍ Scribed by A.R. Dunn; R.J. Stoodley

Book ID
104229889
Publisher
Elsevier Science
Year
1969
Tongue
French
Weight
257 KB
Volume
10
Category
Article
ISSN
0040-4039

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✦ Synopsis

Recently (1) we reported the preparation of (69 3_carbomethov-4-thia-1-azabicyclo[4.1.0] hept-2-ene (I). This compound is of interest since its groundand excited-state properties should provide a measure of the interaction of the aziridine ring with the r-electrons. For example, the UV spectrum of I (EtOH) shows not only an absorption maximum at 230 run (~6,500)

attributable to the @-unsaturated ester chromophore (Z), but also a daxirmm at 298 nm (L 7,700)

(3) indicating that either the nitrogen lone pair or the three-membered ring is extending the conjugation of the n-system. H 5a '6 In principle I may exist in one of two conformations represented by Ia and Ib. Conjugation

πŸ“œ SIMILAR VOLUMES

Rearrangement of a Bicyclo[3.2.0]hept-2-
Rearrangement of a Bicyclo[3.2.0]hept-2-ene to a Bicyclo[4.1.0]hept-4-ene
✍ Behrendt, Uwe ;Gabor, Barbara ;Mynott, Richard ;ButenschΓΆn, Holger πŸ“‚ Article πŸ“… 2006 πŸ› John Wiley and Sons 🌐 English βš– 996 KB

## Abstract The chemistry of the highly substituted cyclobutanone derivative 2, which is easily accessible from 1, is dominated by the steric hindrance caused by the substitutents: Reduction with hydride reagents and nucleophilic additions with methyllithium are less stereoselective than correspond