2,4,6-Triphenylphosphabenzene

✍ Scribed by Dr. G. Märkl

• Publisher: John Wiley and Sons
• Year: 1966
• Tongue: English
• Weight: 225 KB
• Volume: 5
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.196608463

✦ Synopsis

1,3-Diphenylbenzo[c]furan ( I ) has proved of particular

value for the detection of lower-membered cycloalkynes [I]. In order to ascertain that it is cyclohexyne which is trapped, in accordance with equation (a), and not perhaps 1,2-cyclohexadiene, we have generated the cyclic allene by an independent route and allowed it to react with ( I ) . Sublimed potassium t-butoxide was treated with l-bromocyclohexene in dimethyl sulfoxide in the presence of ( I ) for several hours at 40OC. Chromatography on A1203 then gave, among other products, two compounds, ( 3 4 (m.p. 137-138 "C) and (3b) (m.p. 195-196 "C), in a total yield of 37 %; these are isomers of compound (2) (m.p. 170-171 "C)