Phase Transfer Catalysis: An Interim Project We have found that experiments in phase transfer catalysis (PTC) provide students with a very profitable interim project in our 4-1-4curriculum. In a recent interim period, students of varying background, ranging from one semester of organic chemistry to senior chemistry majors participated in a research-oriented PTC project. The students were given references to several papers in recent literature and were asked to repeat the reported experiment. During the early part of the term, papers were chosen which contained detailed experimental sections. However, some of the later papers were short communications which required the student t o design his experimental procedure. The equipment required for the PTC is quite simple. Most reactions can be conducted in small Erlenmeyer flasks equipped with a magnetic stirrer. Work-ups consist mainly of separation and distillation or crystallization of the products. The reaction time for many PTC experiments is quite short and many produce high yields of a single product. Thus, phase transfer catalysis offers the beginning student an ideal entry into a research oriented situation. During our interim term, some of the experiments conducted included the addition of dichlorocarbene to cyclohexene ( I ) , preparation of alkyl nitriles (21, purple benzene oxidations (3).preparation of thio ethers (these experiments are best conducted under an efficient hood) ( 4 ) . and preparation of phenolic ethers (5). In this project quanternary ammonium salts and m i n e s were used as catalysts. While the crown ethers are very effective catalysts, the cost was prohibitive in this case. Students entering this project received a two hour seminar on PTC prior t o any laboratory work. Numerous reading assignments from review articles and from same of the more basic papers were also required (6).
Literature Cited Mskosla, M., and Waanynievicz, M., Tdrohsdron Lett.. 4659 11969); Issgswe, K.,Kimurs, Y. and Kwon, S., J. Olg. Chsm., 39.3171 (1974. Reeven..W.P..and White.M.R.. 119761. . ,Svnlhoriecomm.. . . 6.193 . D., ~ ~ t L ~ ~~ I1511 . ,~ 1 1 h 9 ~~ d ~ ~ ~ ~ ~ ~ A. i w., ~ t t picker, , Landini, D.,end Rolia, F.,Synthesis. 565 (1974). Mekillop,A..Fisud.J. C..and Hug,R. P., Tetmhsdron 30, 1379(1974). (6) Starks.C.M..J.Amcr Cham. Snc. 91,196(1971):Starks.C.M.andOuens,R.M., JAmer. Chem. Soc.. 95,36111197~);Dakx,J.,Synlhrris. 441 11978);Dehmlou, E.V.,Angsw. Chem Internot. E d E n g l . , 13.170 11974).
(1) 121 i3j (4) (51
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Texas Lutheran College Seguin, Texas 78155
W. Preston Reeves
Volume 55, Number 7,July 1978 1 433
