The cleavage of ethers by benzyne

✍ Scribed by Gary D. Richmond; Wolfgang Spendel

• Book ID: 104238606
• Publisher: Elsevier Science
• Year: 1973
• Tongue: French
• Weight: 209 KB
• Volume: 14
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)87275-0

✦ Synopsis

Recently, reports have appeared which describe the cleavage of diethyl ether with highly electrophillc tetrachlorobenzyne and tetrafluorobenzyne to give ethylene and the corresponding 2,3,4,5-tetr&alophenetole. 192 Although unsubstituted benzyne is thought to undergo nucleophlllc attack by ethers to form betaines, no cleavage products have been isolated in the absence of betalne-trapping reagents. 293 In contrast we wish to report the facile cleavage of ethers by benzyne in a solvent medium other than the ether itself.

Yhen benzenediazonlum-2-carboxylate (O.l3m), isolated as a slurry In 200 ml of chloro-