Hypoiodite thermolysis–cyclization reaction. Convenient synthesis of 4-homoprotoadamantan-4-one (tricyclo[5.3.1.03,9]undecan-4-one) from 3-homoadamantanol

Thermolysis of 3-homoadamantyl hypoiodite followed by base-promoted intramolecular cyclization yields 78% of a 3:2 mixture of 4-homoadamantanone and the hitherto unknown 4-homoprotoadamantan-4-one (tricyclo[5.3.1.03,9]undecan-4-one).