Mechanism of the Wolff rearrangement of α-diazohomoadamantanone: evidence against oxiren participation

Abstract

Photolysis of 5-diazo[5-¹⁴C]homoadamantan-4-one in aqueous tetrahydrofuran leads to adamantane 2-carboxylic acid with only 0·9% of the label in the carboxylic group indicating that oxiren participation is insignificant in the Wolff rearrangement of this polycyclic system.