Ozonides of mono-, bi- and tricyclic terpenes

Ozonolysis of (+)-limonene (1) afforded a monoozonide 2 by attack of ozone at the internal double bond and two diastereomeric diozonides (3). Ozonolysis of 1 on polyethylene gave diozonides 3, and ozonolysis on silica gel gave an epoxy ozonide 5. Ozonolyses of (-)-beta-pinene (15), (+)-sabinene (20) and (+)-aromadendrene (23) gave two diastereomers, each, of the corresponding ozonides 16, 21 and 24, respectively. Ozonolysis of camphene (26) gave a very labile ozonide 27, while ozonolysis of (-)-alpha-pinene (12) gave no ozonide. Ozonolysis of (+)limonene (1) in the presence of formaldehyde gave a cross-ozonide (4), derived from ozone cleavage of the internal double bond, and ozonolysis of (-)-beta-pinene in the presence of acetaldehyde also gave a cross-ozonide (17). Copyright (C) 1996 Elsevier Science Ltd