Addition of dibromocarbene to tricyclo[3.2.1.02,4]oct-6-enes. The tricyclo[3.3.1.02,4]non-6-ene ring system.
โ Scribed by Raymond A. Baylouny; Katherine Hankovsky; David Kates; John P. Sibilia
- Publisher
- Elsevier Science
- Year
- 1970
- Tongue
- French
- Weight
- 200 KB
- Volume
- 11
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The addition of dihalocarbenes to norbornene and Its derivatives produces an lntermdiate which Imdergoes a cyclopropyl-ally1 rearrangement. (2) The gem-dihalocyclopropane, Isolated in
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In the preceding cosxnunication,l we noted that the ozonoly~is of 6,7-dimethoxy-exo--tricyclcf3.2.1.02'4]oct-6-ene (1) in methanol gave 7,7-dimethoxy-z-tricycq3.2.1.02'~act-6-one (2), in addition to the expected osonolysis product 3. We now wieh to report -our mechanistic studies related to this eno
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We report a striking example of unprecedented regiospecificity in the addition of acetic acid to endo-tricyclo[3.2.1.0z"]oct-6-ene (1). The addition proceeds with surprising ease in acetic acid at 80' (3 days) or at room temperature in the presence of catalytic amounts of toluenesulphonic acid to yi