Trimethylsilylazide/KN₃/18-Crown-6. Formation and Curtius Rearrangement of Acyl Azides from Unreactive Acid Chlorides

References

• Washburne , S. S. and Peterson , W. R. Jr. 1972 . Syn. Commun. , 2 : 227 S. S. Washburne, W. R. Peterson, Jr., and D. A. Berman, J. Org. Chem. 37, 1738 (1972). J. H. MacMillan and S. S. Washburne, J. Org. Chem., 38, 2982 (1973). J. D. Warren, J. H. MacMillan and S. S. Washburne, J. Org. Chem., 40, 743 (1975). J. H. MacMillan and S. S. Washburne, J. Heterocycl. Chem. 12, 1215 (1975)
   Google Scholar
• Smith , P. A. S. 1946 . Org. Reactions , 3 : 337
   Google Scholar
• Evans , D. A. and Truesdale , L. K. 1973 . Tet. Lett. , 49 : 4929 The insertion of TMSA into aldehyde carbonyls, catalyzed by a preformed KN3·18-Crown-6 complex, has been described by
   Google Scholar
• Bunce , S. C. and Clark , J. B. 1954 . J. Amer. Chem. Soc. , 76 : 2444 This three-step synthesis of VII proceeds from commercially available 1-phenylcyclopropylcarbonitrile in ca. 27% yield. In contrast, our method represents a more advantageous preparation of VII from commercially available material.5
   Google Scholar
• Acid chloride I was prepared from 1-phenylcyclopropylcarboxylic acid in 95% yield by heating it with thionyl chloride in benzene, followed by evaporation of the solution and bulb to bulb distillation of the product
   Google Scholar
• Press , J. B. , Hofmann , C. M. and Safir , S. R. 1979 . J. Org. Chem. , 44 : 0000
   Google Scholar
• Press , J. B. and Safir , S. R. U. S. Patent . 4,144,235 . March 13, 1979 .
   Google Scholar