Conformational analysis. XI. 2-Carbomethoxy-7-oxabicyclo[2.2.1]heptane and 2-carbomethoxy-7-oxabicyclo[2.2.1]hept-5-ene
β Scribed by Ouellette, Robert J.; Rosenblum, Annette; Booth, Gary
- Book ID
- 127051850
- Publisher
- American Chemical Society
- Year
- 1968
- Tongue
- English
- Weight
- 305 KB
- Volume
- 33
- Category
- Article
- ISSN
- 0022-3263
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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,)~.
## Abstract Radical addition to 7βoxabicylco[2.2.1]heptβ5βenβ2βone (1) was examined from a regiochemical point of view, and despite the small electronic anisotropy of the double bond, electrophilic radicals were found to add preferentially at C(5) with selectivities of up to 5:1. We also report the