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Disproportionation versus dianion intermediacy in alkali metal reduction of saturated and unsaturated ketones

✍ Scribed by Suresh K. Pradhan; Shrikant S. Sakhalkar

Publisher: Elsevier Science
Year: 1993
Tongue: French
Weight: 291 KB
Volume: 34
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)91789-1

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✦ Synopsis

Reduction of tj-methyl-4,5-secoandrost3-yn-5-en-7-one, 1, to 5 p-methyl-4,5-secoandrost-3-yn-7-one, 4, is shown by deuterium labelling to proceed via 7 hydrogen transfer when CloHsNa is used whereas Na/NH3 traps the intermediate radical anion by reduction to a dianion.

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Ketone dianions, ketone-ketyl coupling,

Ketone dianions, ketone-ketyl coupling, and possible reaction-during-mixing effects in alkali metal/ammonia reductions of saturated ketones

✍ Valentin Rautenstrauch 📂 Article 📅 1988 🏛 Elsevier Science 🌐 French ⚖ 397 KB

The hypothesis of Pradhan that alkali metal/NH3 reductions of saturated ketones lead to ketone &anions which then deprotonate unreacted ketone can be excluded because the dianions would have been protonated in experiments in which 50-110 equiv of tert.-Bush, Et&L, and H20 were present in the reactio