133752-75-7Relevant articles and documents
Crown Ethers from o-Quinone Diazides and Oxetane
Kirmse, Wolfgang,Lelgemann, Rudolf
, p. 1865 - 1866 (2007/10/02)
The carbenes 11, generated by photolysis of the di- and tetrachloro-o-quinone diazides 10, react with oxetane in a 1:3 ratio to give the 15-membered crown ethers 19.In the presence of methanol, the oxonium ions 12 are trapped with formation of 1-(aryloxy)-3-methoxypropanes (13).In the absence of additional nucleophiles, 12 react with oxetane until the chain length is appropriate for inverting intramolecular attack of the aryl oxide at the α-carbon atom of the oxonium ion (18 -> 19). Key Words: Carbonyl carbenes/ Oxygen ylides/ Displacement, nucleophilic, intramolecular/ Carbenes/ Ylides