An Efficient Conversion of N-Alkyllactams to N-Alkylthiolactams

References

• Kaloustian , M. K. and Khouri , L. 1982 . Tetrahedron Lett. , 23 : 743 The Chemistry of Tetrahedral Intermediates. Part 10. Part 9
   Web of Science ®Google Scholar
• J. J. B. at the American Chemical Society's 29th Annual Regional Undergraduate Research Symposium . May 2 , N. Y. : State University of New York . Purchase
   Google Scholar
• Woodward , R. B. 1973 . Pure Appl. Chem. , 33 : 145 – 177 .
   PubMedGoogle Scholar
• Eschenmoser , A. 1971 . Pure Appl. Chem. , 25 : 69 Suppl.
   Google Scholar
• Scheeren , J. W. , Ooms , P. H. J. and Nivard , R. J. F. 1973 . Synthesis , : 149
   Web of Science ®Google Scholar
• Renson , M. and Collienne , R. 1964 . Bull. Soc. Chim. Belges , 73 : 491
   Google Scholar
• Ogata , M. and Matsumoto , H. 1978 . Heterocycles , 11 : 139
   Web of Science ®Google Scholar
• Scheibye , S. , Pedersen , B. S. and Lawesson , S.-O. 1978 . Bull. Soc. Chim. Belges , 87 : 229
   Google Scholar
• Kaloustian , M. K. and Khouri , F. 1981 . Tetrahedron Lett. , 22 : 413
   Web of Science ®Google Scholar
• Meerwein , H. , Porner , P. , Fuchs , O. , Sasse , H.-J. , Schrodt , H. and Spille , J. 1956 . Chem. Ber. , 89 : 2060
   Google Scholar
• Meerwein , H. , Florian , W. , Schön , N. and Stopp , G. 1961 . Justus Liebigs Ann. Chem. , 641 : 1
   Google Scholar
• Eibeck , R. E. 1963 . Inorg. Syn. , 7 : 128
   Web of Science ®Google Scholar
• We have successfully effected the sulfhydrolytic step of Method A (e.g. on 4 and 5) at temperatures as low as -78°C, with comparable yields.
   Google Scholar
• The Rf values of9–13 are 0.51, 0.43, 0.47, 0.50, and 0.49, respectively, vs. 0.17, 0.18, 0.17, 0.20, and 0.25, respectively, for the corresponding O-analogs (all in CH2Cl2)
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• The calculated amount of NaSH should be added in portions, and at the lowest possible temperature.
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• The application of Method A to O-methyl-λ-butyro-lactamium fluoroborate, gave only 14° yield of thiolactam; the recovered imino ether was identical with authentic sample prepared from the lactamium salt by treatment with NaH (Et2O, 27°C, 1 hr). Bubbling H2S prior to step 2 (Method A) did not help.
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• Pesco , A. and Kaloustian , M. K. unpublished results
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