References
- Stork , G. and Danheiser , R. L. 1973 . J. Org. Chem. , 38 : 1776
- Wittig , G. , Boll , W. and Kruch , K. H. 1962 . Chem. Ber. , 95 : 2514
- Corey , E. J. and Shulman , J. I. 1970 . J. Amer. Chem. Soc. , 92 : 5522
- Adams , J. , Hoffman , L. and Trost , B. M. 1970 . J. Org. Chem. , 35 : 1600
- Jones , P. F. and Lappert , M. F. 1972 . Chem. Comm. , : 526
- Grosserode , R. S. , Tobin , P. S. and Wheeler , D. M. S. 1976 . Syn. Comm. , 6 : 377 The latter paper describes a method of preparing methyl ketones similar to that described herein
- We have found the 3-ethoxy substituent to be technically somewhat better to handle than the 3-isobutyl analogues reported by Stork (reference 1)
- Bis(methylthio)methyllithium is easily generated by treatment of bis(methylthio)methane with n-butyllithium in THF at 0° followed by stirring at this temperature for 30 minutes
- The yields of these adducts ranged from 80 to 95%. Their purity was determined by GC and nmr
- In all cases the 3-formyl-cycloalkenones prepared in this manner were obtained in greater than 95% purity directly from the reaction mixture (determined by GC, nmr, and mass spec). Distillation of these compounds may be used as a method of purification. The boiling points of these materials ranged between 60° and 75° at 0.5 torr