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A curious benzenoid deacylation reaction: neighbouring group participation in acylhydroxy[2.2]paracyclophanes

โœ Scribed by D.Christopher Braddock; Iain D MacGilp; Benjamin G Perry

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
62 KB
Volume
42
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Attempted carbonyl reduction of acyldihydroxy[2.2]paracyclophanes with sodium borohydride led instead to competing aromatic deacylation. The effect was traced to a neighbouring group participation that can be correlated with carbonyl IR stretching frequencies. Deuterium labelling studies implicate the formal intermediacy of a solvated [2.2]paracyclophane anion via an S E 1 mechanism.

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