The stereochemistry was studied concerning the ring expansion of some 2-isopropenylcyclopropane-1-carbonyl compounds to 2,5-dihydro-3-methyloxepin derivatives. The LAH reduction of dimethyl 2-isopropenylcyclopropane-1,1-dicarboxylate (1aa) gave the corresponding diol, and a subsequent Swern oxidation gave a seven-membered 4,7-dihydro-6-methyloxepin-3-carbaldehyde. A DIBAL reduction of 1aa gave two isomeric hydroxymethyl carboxylic esters, and a subsequent Swern oxidation of methyl 1-hydroxymethyl-t-2-isopropenylcyclopropane-r-1-carboxylate caused a ring expansion to give methyl 4,7-dihydro-6-methyloxepin-3-carboxylate; however, a similar Swern oxidation of methyl 1-hydroxymethyl-c-2-isopropenyl-cyclopropane-r-1-carboxylate caused no ring expansion to give methyl 1-formyl-c-2-isopropenylcyclopropane-r-1-carboxylate.
Die Reaktion der Nitrile (I) mit dem Sulfoxid (II) führt in Gegenwart von Natriumhydrid zu den Verbindungen (III), die sich mit den Anhydriden (IV) und Pyridin in (V) überführen lassen.
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