120428-78-6Relevant articles and documents
The Cyclopropane-Mediated Ring-Expansion of Propellenes. A New Route to <5.3.1)Propelladienes
Banwell, Martin G.
, p. 1037 - 1049 (2007/10/02)
The propelladiene (1) has been synthesized in six steps from the readily avalaible propellene (10a).Epoxidation of (10a) gives oxide (11a) which undergoes base-promoted rearrangement to allylic alcohol (12a).Simmons-Smith cyclopropanation of (12a) then gives the tetracyclic alcohol (13a).Mild thermolysis of the derived mesylate (14a) affords the ring-expanded isomer (20) which reacts with 1,8-diazabicycloundec-7-ene to give diene (1).A similar sequence of reactions has been used in the preparation of dienol (2) from acetal (10b).Compounds (1) and (2) react with 4-phenyl-4H-1,2,4-triazoline-3,5-dione to give the Diels-Alder adducts (29a) and (29b) respectively.