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The Preparation of Optically Pure 7-Oxabicyclo [2.2.1]hept-2-ene Derivatives. The CD Spectrum of (+)-(1R)-7-Oxabicyclo [2.2.1]hept-5-en-2-one

✍ Scribed by Eric Vieira; Pierre Vogel

Publisher: John Wiley and Sons
Year: 1983
Tongue: German
Weight: 408 KB
Volume: 66
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19830660627

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✦ Synopsis

Dedicated to Prof. Ch. Tamm on the occasion of his 60th birthday (12.4.83)

Summary

(-)-1-Camphanoyloxyacrylonitrile (= (-)-1 -cyanovinyl camphanate; 1) obtained from the commercially available ( -)-camphanoyl chloride and 2-0x0propiononitrile added to furan at 20" in the presence of CU(BF,)~. 6 H 2 0 or Zn12 and gave a mixture of 2-cyano-7-oxabicyclo [2.2. IIhept-5-en-2-yl camphanates (2-5) from which isomer 5 could be obtained pure by crystallization. The latter was transformed into (+ )-( 1 R)-7-oxabicyclo [2.2.1]hept-5-en-2-one (6) in high yield and optical purity. Adducts 2-4 were recycled into 1 + furan by heating in toluene, and (-)-camphanic acid was recovered after saponification of 5. The absolute configuration of 6 was deduced from its CD spectrum which showed two 1200-cm-' Franck-Condon series for its n + nEo transition.

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