M. Oda*, Yoshimi Masaki, Yoshimichi Okazaki
Aug 1, 1998
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Journal
Bulletin of the Chemical Society of Japan
Abstract
Reaction of tricyclo[5.3.1.01,7]undeca-2,4,9-triene with butyllithium in tetrahydrofuran-hexamethylphosphoric triamide at −78 °C and subsequent quenching of the resulted dark red reaction mixture with water or methanol gave tricyclo[6.3.0.01,3]undeca-5,7,9-triene (4) as the sole isolable product. It was also found that quenching of the anion solution with deuterium oxide under the same conditions caused stereoselective incorporation of deuterium atom. On the other hand, quenching of the anion solution with water after it was warmed to 0 °C gave a mixture of dihydromethylazulenes. The cycloadduct of the rearranged hydrocarbon 4 with 4-phenyl-3H-1,2,4-triazoline-3,5(4H)-dione was obtained and its structure was confirmed by X-ray crystallographic analysis. A driving force of the circumambulation was thought to be the creation of conjugation between the cycloheptadienide part and the five-membered ring olefin in the product on the basis of the facts that a circumambulatory rearrangement in the opposite direct...