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Cyclisation versus elimination reactions in a neighbouring group system

โœ Scribed by F.L. Scott; A.F. Hegarty; R.J. MacConaill

Publisher
Elsevier Science
Year
1972
Tongue
French
Weight
223 KB
Volume
13
Category
Article
ISSN
0040-4039

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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 t