(Chlorosulfinyloxy)-N,N-dimethylmethaniminium Chloride Mediated Direct and Chemoselective Conversion of Carboxylic Acids into Aldehydes

(Note: The full text of this document is currently only available in the PDF Version )

R. H. Khan and T. S. R. Prasada Rao


Abstract

A new method for the direct conversion of carboxylic acids into aldehydes using (chlorosulfinyloxy)N,N-dimethylmethaniminium chloride and lithium triethylhydroborate (super-hydride) was established which provides a convenient way for the chemoselective reduction of carboxylic acids even with such functional groups as halide, ester, nitrile, olefin and ketone.


References

  1. E. Mosettig and R. Mozingo, Org. React., 1948, 4, 363.
  2. H. C. Brown and B. C. Subba Roa, J. Am. Chem. Soc., 1958, 80, 5377 CrossRef CAS; G. W. T. Fleet and P. J. C. Hording, Tetrahedron Lett., 1980, 21, 813 CrossRef; T. N. Sorrell and P. S. Pearlman, J. Org. Chem., 1980, 45, 3449 CrossRef.
  3. H. C. Brown and A. Tsukamoto, J. Am. Chem. Soc., 1961, 83, 4549 CrossRef CAS; M. Murakai and T. Mukaiyama, Chem. Lett., 1975, 875.
  4. M. Muraki and T. Mukaiyama, Chem. Lett., 1975, 215 CAS; R. Kanazawa and T. Tokoroyama, Synthesis, 1976, 526 CrossRef CAS.
  5. G. Doleschall, Tetrahedron, 1976, 32, 2549 CrossRef CAS; N. S. Ramegowda, M. N. Modi, A. K. Koul, J. M. Bora, C. K. Narang and N. K. Mathur, Tetrahedron, 1973, 29, 3985 CrossRef CAS; T. Izawa and T. Mukaiyama, Bull. Chem. Soc. Jpn., 1979, 52, 555 CAS; J. C. Craig, N. N. Ekwuribe, C. C. Fu and K. A. M. Walker, Synthesis, 1981, 303 CrossRef CAS.
  6. E. Mosettig, Org. React., 1954, 8, 218.
  7. A. O. Bedenbaugh, J. H. Bedenbough, A. Bergin and J. D. Adkins, J. Am. Chem. Soc., 1970, 92, 5774 CrossRef CAS.
  8. M. Muraki and T. Mukaiyama, Chem. Lett., 1974, 1447 CAS.
  9. H. C. Brown, P. Heim and N. M. Yoon, J. Org. Chem., 1972, 37, 2942 CrossRef CAS.
  10. F. Sato, T. Jinbo and M. Sato, Synthesis, 1981, 871 CrossRef CAS.
  11. A. Arrieta, J. M. Azipurua and C. Palomo, Tetrahedron Lett., 1984, 25, 3365 CrossRef CAS; M. Ballester, J. Riera, J. Castaner, C. Rovira, J. Veciano and C. Onrubia, J. Org. Chem., 1983, 48, 3716 CrossRef CAS.
  12. H. Bosshard, R. Mory, M. Schmid and Hch Zollinger, Helv. Chim. Acta, 1959, 42, 1653 CAS.
  13. A. L. Palomo and G. Ferrer, An. Quim., 1969, 65, 163 (Chem. Abstr., 1969, 71, 2844) Search PubMed.
  14. M. S. Newman and P. K. Sujeeth, J. Org. Chem., 1978, 43, 4367 CrossRef CAS.
  15. S. P. Singh, A. R. Mahajan, D. Projapati and J. S. Sandhu, Synthesis, 1991, 1026 CrossRef CAS.