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Abstract
Nucleophilic addition of diazomethane to sym-trinitrobenzene (TNB) in a molar ratio 1:3 leads via ring expansion to trismethylene-TNB (I), a seven-membered ring compound condensed with two cyclopropane rings (scheme 1). The double bond in trismethylene-TNB is broken by dichromate (scheme 2), ozone (scheme 5) and alkaline permanganate (scheme 6). In the latter case an α-hydroxy acid is formed via an extremely facile rearrangement in which the seven-membered ring contracts to a six-membered one (scheme 7). The process can be repeated to give an α-hydroxy acid with a five-membered ring (scheme 8). A trismethylene derivative (XX) can also be obtained from picric acid (scheme 18), but the cyclopropane rings are condensed with the seven-membered ring in a stereochemically different way. The product does not rearrange with permanganate, but an isomeric trismethylene derivative (XXIV) does so (scheme 21).
Published Version
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