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Benzoenynes-allenes

Scheme 3.48. Thermolysis of benzoenynes-allenes initiating a domino radical cyclization. Scheme 3.48. Thermolysis of benzoenynes-allenes initiating a domino radical cyclization.
The synthesis of polycyclic aromatic compounds from substituted propargylic alcohols is based on a cascade cyclization initiated by the action of thionyl chloride (in pyridine) proceeding, apparently, via a diradical generated from the intermediate chlorinated benzoenyne-allene [279, 280]. The synthesis of benzannulated enyne-allene has been successfully achieved using the Claisen rearrangement of propargylic alcohol acetates. This route was used for the direct synthesis of several... [Pg.143]

A new synthetic pathway to generate the chlorosubstituted benzoenyne-allenes in situ for the subsequent cascade radical cyclizations was established. This pathway was adopted for the preparation of the C44H26 hydrocarbon having a carbon framework represented on the surface of Cgo. Using different combinations of benzoenediynes and diaryl ketones for condensation, it is possible that a variety of other polycyclic aromatic hydrocarbons could also be likewise synthesized [280]. [Pg.146]

Li, H., Zhang, H.-R., Petersen, J.L. and Wang, K.K. (2001 Biradicals from benzoenyne-allenes. Application in the synthesis of 1 lff-benzo[f>]fluoren-1 l-ols,lff-cyclobut[a]indenes, and related compounds. Journal of Organic Chemistry, 66(20), 6662-6668. [Pg.274]


See also in sourсe #XX -- [ Pg.251 ]

See also in sourсe #XX -- [ Pg.251 ]




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