Regiospecific addition of TCNE to 2-exo-methyl-endo-tricyclo [3.2.1.02,4] oct-6-ene
โ Scribed by J.M. Coxon; M. de Bruijn; C.K. Lau
- Publisher
- Elsevier Science
- Year
- 1975
- Tongue
- French
- Weight
- 173 KB
- Volume
- 16
- Category
- Article
- ISSN
- 0040-4039
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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
The addition of dihalocarbenes to norbornene and Its derivatives produces an lntermdiate which Imdergoes a cyclopropyl-ally1 rearrangement. (2) The gem-dihalocyclopropane, Isolated in
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