Journal of Organic Chemistry p. 2916 - 2920 (1981)
Update date:2022-08-04
Topics:
Kagan, Jacques
Agdeppa, Dalmacio A.
Chang, Arthur I.
Chen, Shyi-An
Harmata, Michael A.
et al.
The treatment of phenylacetaldehydes in fluorosulfuric acid generates 2,3,6,7-dibenzo-9-oxabicyclo<3.3.1>nona-2,6-dienes.The generality of this reaction was tested on several derivatives which were substituted either at the 2-position or on the ring.Diastereoisomers, whenever obtained, were characterized by a combination of X-ray analysis and NMR data.Phenylacetone reacted differently and afforded the products of electrophilic aromatic substitution by fluorosulfuric acid.The structure of the unexpected minor reaction products was elucidated.
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