Journal of the Chemical Society. Perkin transactions I p. 1462 - 1472 (1980)
Update date:2022-08-05
Topics:
Jemison, Robert W.
Ollis, W. David
Sutherland, Ian O.
Tannock, James
The <1,3> sighmatropic rearrangement (11) -> (12) of the 9-dimethylamino-9-(1-phenylallyl)fluorene is a stereoselective process (84:16) at 170 deg C.Analogous <1,3> rearrangements (16) -> (17) of the fluorene derivatives show that the reaction rate is increased by electron donating 9-substituents in the order O- > NMe2 > OMe.Similar substituent effects are observed for the <3,3> Cope rearrangement (25) -> (26) of hexa-1,5-dienes. 4-Phenyl, 4,4-dimethyl, and 3-dimethylamino substituents are particularly effective in accelerating the rate of the rearrangement (25) -> (26).
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Doi:10.1055/s-1980-29122
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