LIGAND EXCHANGE AND LIGAND COUPLING VIA THE σ-SULFURANE INTERMEDIATE IN THE REACTION OF ALKYL 2-PYRIDYL SULFOXIDE WITH GRIGNARD REAGENTS: CONVENIENT PREPARATION OF 2,2′-BIPYRIDINES

References

• Kawai , T. , Furukawa , N. and Oae , S. 1984 . Tetahedron Lett. , 25 : 2546 Preliminary communication, see
   Google Scholar
• Oae , S. , Kawai , T. and Furukawa , N. 1984 . Tetrahedron Lett. , 25 : 69
   Web of Science ®Google Scholar
• Oae , S. , Kawai , T. , Furukawa , N. and Iwasaki , F. 1987 . J. Chem. Soc. Perkin Trans II , : 405
   Google Scholar
• Khim , Y. H. and Oae , S. 1969 . Bull. Chem. Soc. Jpn. , 42 : 1968
   Web of Science ®Google Scholar
• Andersen , K. K. , Yeager , S. A. and Peynircioglu , N. B. 1970 . Tetrahedron Lett. , : 2485
   Google Scholar
• Ackerman , B. K. , Andersen , K. K. , Karup-Nielsen , I. , Peynircioglu , N. B. and Yeager , S. A. 1974 . J. Org. Chem. , 39 : 964
   Web of Science ®Google Scholar
• Trost , B. M. , La Rochelle , R. W. and Atkins , R. C. 1969 . J. Am. Chem. Soc. , 91 : 2175
   Web of Science ®Google Scholar
• La Rochelle , R. W. and Trost , B. M. 1971 . J. Am. Chem. Soc. , 93 : 6077
   Web of Science ®Google Scholar
• Trost , B. M. and Arndt , H. C. 1973 . J. Am. Chem. Soc. , 95 : 5288
   Web of Science ®Google Scholar
• Oae , S. , Yoshimura , T. and Furukawa , N. 1972 . Bull. Chem. Soc. Jpn. , 45 : 2019
   Web of Science ®Google Scholar
• Sheppard , W. A. 1971 . J. Am. Chem. Soc. , 93 : 5597
   Web of Science ®Google Scholar
• Hori , M. , Kataoka , T. and Shimizu , H. 1973 . Yakugaku-Zashi , 93 : 476 idem. Chem. Pharm. Bull., 22, 1711, 2004, 2014, 2020, 2030 (1974).
   PubMed Web of Science ®Google Scholar
• Lockard , J. P. , Schroeck , C. W. and Johnson , C. R. 1973 . Synthesis , : 485
   Web of Science ®Google Scholar
• Hojo , M. , Masuda , R. , Saeki , T. , Fujimori , K. and Tsutsumi , S. 1977 . Synthesis , : 789
   Web of Science ®Google Scholar
• Oda , R. and Yamamoto , K. 1961 . J. Org. Chem. , 26 : 4679
   Web of Science ®Google Scholar
• Tsuchihashi , G. , Iriuchigima , S. and Ishibashi , M. 1972 . Tetrahedron Lett. , : 4605
   Google Scholar
• Bernardi , F. , Csismadia , I. G. and Mangini , A. , eds. 1985 . “Non-bonded Sulfur-Oxygen Interaction in Organic Sulfur Compounds” by A. Kucsman and I. Kapovits and in Chapter 8, “Sulfurane Chemistry”, by R. A. Hayes and J. C. Martin ” . In “Organic Sulfur Chemistry” , Elsevier . see many references in Chapter 4
   Google Scholar
• Hamilton , W. C. and Laplaca , S. J. 1964 . J. Am. Chem. Soc. , 86 : 2289
   Web of Science ®Google Scholar
• Wittig , G. 1964 . Pure Appl. Chem. , 9 : 245 – 254 . For the historical background, see
   Google Scholar
• Harpp , D. N. , Vines , S. M. , Montillier , J. P. and Chan , T. H. 1976 . J. Org. Chem. , 41 : 3987
   Web of Science ®Google Scholar
• Newkome , G. R. and Hager , D. C. 1978 . J. Am. Chem. Soc. , 100 : 5567
   Web of Science ®Google Scholar
• Several unpublished examples to show the facile coupling of benzylic and allylic groups with heteroaryl or aryl groups bearing an electron-withdrawing substituent have been accumulated in these laboratries.
   Google Scholar
• Direct nucleophilic substitution of phenyl at the 2-position of pyridine may not be the plausible path, since our preliminary result on the reaction between t-butyl 2-pyridyl sulfoxide with CH3CH2MgBr gave both 2-ethylpyridine and a small amount of 2-t-butylpyridine.
   Google Scholar
• Furukawa , N. , Takahashi , F. , Kawai , T. , Kishimoto , K. , Ogawa , S. and Oae , S. 1983 . Phosphorus and Sulfur , 16 : 167
   Web of Science ®Google Scholar
• Gilman , H. and Spatz , S. M. 1951 . J. Org. Chem. , 16 : 1485
   Web of Science ®Google Scholar
• Maki , T. and Takahashi , T. 1966 . Japan P , 19 : 070 Chem. Abstracts, 66, 37936y (1967)
   Web of Science ®Google Scholar
• Furukawa , N. , Ogawa , S. , Kawai , T. and Oae , S. 1984 . J. Chem. Soc. Perkin Trans. 1 , : 1839
   Google Scholar
• Case , F. H. 1946 . J. Am. Chem. Soc. , 68 : 2574
   Web of Science ®Google Scholar
• Ogawa , S. and Shiraishi , S. 1980 . J. Chem. Soc., Perkin Trans 1 , : 2527
   Google Scholar
• Parks , J. E. , Wagner , B. E. and Holm , R. H. 1973 . J. Organomet. Chem. , 56 : 53
   Web of Science ®Google Scholar
• Saikachi , H. and Hisano , T. 1959 . Yakugaku-Zashi , 79 : 1305
   Google Scholar