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6.1.33.4 Method 4: Oxidation

DOI: 10.1055/sos-SD-006-00799

Kaufmann, D. E.; Burmester, C.Science of Synthesis, (20056919.

A very important conversion of boranes is the oxidation to alcohols by means of alkaline hydrogen peroxide without isomerization (Scheme 8).[‌4‌,‌8‌,‌9‌] Under standard oxidation conditions, propargyl alcohols 13 can be obtained in good yields from boronates 9. If allenic alcohols are also formed, they originate from allenylboranes, which are sometimes formed during the synthesis of the borane. This methodology has frequently been used both to characterize the purity of propargylboranes and also in the total synthesis of the pheromone japonilure.[‌12‌]

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Meeeeeeeeee 8

M8 (MM8)8 Meeee (%) Mee
(MM8)8Me M(MMe8)8M 88 [‌8‌]
8-(8M-eeeee-8-eeeee)eeeee 88 [‌8‌]
MMMM 88 [‌8‌]
(MM8)8Me (MeMe)8 88 [‌8‌]
Me 88 [‌8‌]

References