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IV. Addition of Tin- and Silicon-Centered Radicals to Aldehydes

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    Although the reactions discussed thus far have involved addition of carbon-centered radicals to carbonyl groups, other types of radicals, including tin- and silicon-centered ones, also add to alde­hydes and ketones. Reaction of the tri-n-butyltin radical with a carbonyl group generates a tin ketyl, a radical with con­sid­er­able negative charge on the oxygen atom. As the reac­tion in Scheme 918 shows, tin ketyls undergo internal radical addition to electron-deficient, C–C multiple bonds.18–22 These ketyls also react with C–N double bonds,23 and they produce pinacols upon addition to carbonyl groups (eq 8).24 Internal addition also can occur when a silicon-centered radical adds to an aldehydo group, as happens in the reaction shown in eq 9.25

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    This page titled IV. Addition of Tin- and Silicon-Centered Radicals to Aldehydes is shared under a All Rights Reserved (used with permission) license and was authored, remixed, and/or curated by Roger W. Binkley and Edith R. Binkley.