3,4-Homoadamantadiene: generation and regioselective [2+2] cycloaddition of a novel tricyclic bridgehead allene.
Dehalogenation of 3-bromo-4-iodo-4-homoadamantene with n-BuLi gave rise to 3,4-homoadamantadiene, a novel tricyclic bridgehead allene, which readily dimerized to head-to-head and head-to-tail [2+2] cycloadducts in a ratio of 96:4. Trapping with 1,3-diphenylisobenzofuran was successful to yield the corresponding Diels-Alder adduct.
Ogawa
Kohei
K
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Okazaki
Takao
T
Kinoshita
Tomomi
T