Title of article
A curious benzenoid deacylation reaction: neighbouring group participation in acylhydroxy[2.2]paracyclophanes
Author/Authors
Braddock، نويسنده , , D.Christopher and MacGilp، نويسنده , , Iain D and Perry، نويسنده , , Benjamin G، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2001
Pages
3
From page
7527
To page
7529
Abstract
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 SE1 mechanism.
Keywords
deacylation , neighbouring group participation
Journal title
Tetrahedron Letters
Serial Year
2001
Journal title
Tetrahedron Letters
Record number
1647880
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