P. Camps, F. Luque, M. Orozco
Nov 18, 1996
Citations
0
Influential Citations
25
Citations
Journal
Tetrahedron Letters
Abstract
The synthesis of tricyclo[3.3.0.03,7]oct-1(5)-ene, 5, the consummate member of a series of pyramidalized alkenes, has been carried out by deiodination of 4 in different ways. Reaction of 4 with sodium in boiling dioxane gave in good yield diene 8, whose formation can be easily explained through the intermediacy of 5 and its cyclobutane dimer 6. Reaction of 4 with t-butyllithium in THF at −78 °C in the presence of 1,3-diphenylisobenzofurane gave 10, a Diels-Alder adduct derived from 5.