Marked similarities exist between the mechanism of nitrous acid deamination of B-aminoalcohols and the pinacol rearrangement. Following are examples of each. Nitrous acid NH, NANO, HCI =O + Ng + H,O deamination of a B-aminoalcohol: `OH OH H,SO4 Pinacol СНО + H,О rearrangement: HO,

Marked similarities exist between the mechanism of nitrous acid deamination of B-aminoalcohols and the pinacol rearrangement. Following are examples of each. Nitrous acid NH, NANO, HCI =O + Ng + H,O deamination of a B-aminoalcohol: `OH OH H,SO4 Pinacol СНО + H,О rearrangement: HO,

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter26: Lipids

Section26.6: Fat-soluble Vitamins

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Question

Why does the first reaction, but not the second, give ring expansion?

Marked similarities exist between the mechanism of nitrous acid deamination of
B-aminoalcohols and the pinacol rearrangement. Following are examples of each.
Nitrous acid
NH, NANO, HCI
=O + Ng + H,O
deamination of
a B-aminoalcohol:
`OH
OH H,SO4
Pinacol
СНО + H,О
rearrangement:
HO,

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