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The thermal stability of exo and endo tricyclo[3.2.1.02,4]oct-6-enes and their relevance to the cyclo-addition of cyclopropenes to cyclopentadiene.

✍ Scribed by Charles W. Jefford; Jean-Claude E. Gehret; Jiri Mareda; nTanda Kabengele; W.David Graham; Ulrich Burger


Publisher
Elsevier Science
Year
1975
Tongue
French
Weight
159 KB
Volume
16
Category
Article
ISSN
0040-4039

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✦ Synopsis


As a general rule, cyclopropanes undergo cycle-addition with cyclopentadiene (1) with various degrees of ease to give exclusively the endo adduct'.

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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