Synthesis, Fragmentation, and Rearrangement Reactions of Annelated Cyclobutylcarbinols
04 August 2005 (eFirst)
New tricyclic annelated cyclobutylcarbinols are synthesized diastereoselectively. Acid-induced fragmentation and Wagner-Meerwein rearrangement of these alcohols to give bicyclic dienes and annelated norbornanes are reported.
fused-ring systems - carbocations - rearrangements - ring opening - cycloadditions
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- 5c As already mentioned in ref. 5b the photocycloaddition of cyclopentene to 1 yields a mixture of diastereomers with 2a and its cis,syn,cis-isomer in a 9:1 ratio. For more details see:
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The relative configuration of 2d was determined from 9b by NMR following the reaction sequence 2d Æ 3e Æ 9b.9
The supplementary crystallographic data for this structure (CCDC 237662) can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by e-mailing firstname.lastname@example.org, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.10
The supplementary crystallographic data for this structure (CCDC 237661) can be obtained free of charge as described in ref. 9.