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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 19
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Original Articles

N-(2-Hydroxyalkyl)-2,2-dihaloamides by Amino-de-alkoxylation of Methyl 2,2-Dihalocarboxylates

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Pages 3517-3526 | Published online: 21 Aug 2006

References

  • Frump , J. A. 1971 . Chem. Rev. , 71 : 483
  • Breton , P. , André-Barrè , C. and Langlois , Y. 1992 . Synth. Commun. , : 2543
  • Combret , J.-C. , Tekin , J. and Postaire , D. 1984 . Bull. Soc. Chim. Fr. , II : 371
  • Combret , J.-C. and Tekin , J. 1977 . C. R. Acad. Sci. Paris, Sèrie C , 285 : 249
  • Bretschneider , H. , Piekarski , G. and Biemann , K. 1954 . Monatsh. Chem. , 85 : 882
  • Davis , F. A. and Zhou , P. 1994 . Tetrahedron Lett. , : 7525
  • Schumacher , D. P. , Clark , J. E. , Murphy , B. L. and Fischer , P. A. 1990 . J. Org. Chem. , 55 : 5291
  • Chěnevert , R. and Thiboutot , S. 1989 . Synthesis , : 444
  • Lakshminarayan , N. T. Eur. Pat. Appl. 14,437 . 1980 .
  • 1981 . C. A. , 94 : 139433c
  • Stracke , H. U. , Meins , P. and Schlenzka , E. Ger. Offen. 2,536,975 . 1975 .
  • 1977 . C. A. , 86 : 189194f
  • Cutler , R. A. , Stenger , R. J. and Suter , C. M. 1952 . J. Am. Chem. Soc. , 74 : 5475
  • Surrey , A. R. 1954 . J. Am. Chem. Soc. , 76 : 2214
  • Rebstock , M. C. 1950 . J. Am. Chem. Soc. , 72 : 4800
  • Pansare , S. V. and Ravi , R. G. 1995 . Tetrahedron Lett. , : 5959
  • Myers , A. G. , Yang , B. H. , Chen , H. and Gleason , J. L. 1994 . J. Am. Chem. Soc. , 116 : 9361
  • Najidi , S. , Reichlin , D. and Kurth , M. J. 1990 . J. Org. Chem. , 55 : 6241
  • Marona , H. and Nowak , A. 1988 . Acta Pol. Pharm. , 45 : 105
  • Anteunis , M. J. O. and Becu , C. 1987 . Bull. Soc. Chim. Belg. , 96 : 555
  • Schultz , A. G. , Sundararaman , P. , Macielag , M. , Lavieri , F. P. and Welch , M. 1985 . Tetrahedron Lett. , : 4575
  • Evans , D. A. and Tackacs , J. M. 1980 . Tetrahedron Lett. , : 4233
  • Sonnet , P. E. and Heath , R. R. 1980 . J. Org. Chem. , 45 : 3137
  • Larcheveque , M. , Ignatova , E. and Cuvigny , T. 1977 . J. Organomet. Chem. , 177 : 5
  • Fodor , G. and Kiss , J. 1950 . J. Am. Chem. Soc. , 72 : 3495
  • Welsh , L. H. 1949 . ibid. , 71 : 3500
  • Knorr , L. and Rössler , P. 1903 . Chem. Ber. , 36 : 1278
  • Dodd , J. H. , Guan , J. and Schwender , C. F. 1993 . Synth. Commun. , : 1003
  • Tawaki , S. and Klibanov , A. M. 1993 . Biocatalysis , 8 : 3
  • Fernández , S. , Menéndez , E. and Gotor , V. 1991 . Synthesis , : 713
  • Arai , K. , Tamura , S. , Masumizu , T. , Kaway , K. , Nakajima , S. and Ueda , A. 1990 . Can. J. Chem. , 68 : 903
  • D'Alelio , G. F. and Reid , E. E. 1937 . J. Am. Chem. Soc. , 59 : 111
  • Forti , L. , Ghelfi , F. , Munari , F. and Pagnoni , U. M. 1995 . Tetrahedron , 51 : 12285
  • Lactams became the exclusive products on delaying the reaction time to 67 h
  • McArnett , E. C. , Miller , J. G. and Day , A. R. 1951 . J. Am. Chem. Soc. , 73 : 5393
  • Baltzly , R. , Berger , I. M. and Rothstein , A. A. 1950 . J. Am. Chem. Soc. , 72 : 4149
  • Ratchford , W. P. and Fisher , C. H. 1950 . J. Org. Chem. , 15 : 317
  • Tamelen , E. E. 1951 . J. Am. Chem. Soc. , 73 : 5773
  • Phillips , A. P. and Baltzly , R. 1947 . ibid. , 69 : 200
  • Reasenberg , J. R. and Goldberg , S. D. 1945 . ibid. , 67 : 933
  • Hancock , E. M. and Cope , A. C. 1944 . ibid. , 66 : 1738
  • Cope , A. C. and Hancock , E. M. 1944 . ibid. , 66 : 1448
  • Forti , L. , Ghelfi , F. and Pagnoni , U. M. 1995 . Tetrahedron Lett. , 36 : 3023
  • Bellesia , F. , Boni , M. , Ghelfi , F. and Pagnoni , U. M. 1994 . ibid. , 35 : 2961
  • Boni , M. , Ghelfi , F. , Pagnoni , U. M. and Zucchi , C. 1994 . Bull. Chem. Soc. Jpn. , 67 : 1622
  • Pierce Stanton , J. , Salsbury , J. M. and Fredericksen , J. M. 1942 . J. Am. Chem. Soc. , 64 : 1692
  • Hines , J. and Fischer , C. D. 1975 . J. Am. Chem. Soc. , 97 : 6513
  • The basic washing prevented the rearrangement of N-alkyl-N-(2-hydroxyalkyl)-amides alcohols to corresponding amino esters, which otherwise occurred moderately on standing (in any case N-(2-hydroxyethyl)-N-allyl-2,2dichloro-hedde gave rise to this rearrangement).

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