Efficient Preparation and Resolution of Trans-1,2-cyclobutanedicarboxylic Acid and Some of its Derivatives

References

• Ojima , I , ed. 1993 . Catalytic Asymmetric Synthesis , Weinheim : VCH .
   Google Scholar
• Brunet , J.-J. , Gomez , M. , Hajouji , H. and Neibecker , D. 1993 . Phosphorus, Sulfur & Silicon , 85 : 207
   Web of Science ®Google Scholar
• Aviron-Violet , P. 1975 . Chem. Abs. , 82 : 171186 Ger. Offen., 2 424 543 (Rhône Poulenc);
   Google Scholar
• Aviron-Violet , P. , Colleuille , Y. and Varagnat , J. 1979 . J. Mol. Catal. , 5 : 41
   Google Scholar
• Inouye , Y , Sawada , S. , Ohno , M. and Walborsky , H. M. 1967 . Tetrahedron , 23 : 3237 The (R,R) absolute configuration has been ascribed to the (-)-trans-diacid.
   Google Scholar
• The anhydride of cis-1,2-cyclobutanedicarboxylic acid, as well as 1,2-dicyano cyclobutane and trans-1,2-cyclobutanedicarboxylic acid dichloride were occasionally commercially available from Aldrich or Janssen Chimica.
   Google Scholar
• Misumi , A. , Iwanaga , K. , Furuta , K. and Yamamoto , H. 1985 . J. Am. Chem. Soc. , 107 : 3343
   Web of Science ®Google Scholar
• Furuta , K. , Iwanaga , K. and Yamamoto , H. 1988 . Org. Synth. , 67 : 76
   Google Scholar
• Perkin , W. H. Jr. 1894 . J. Chem. Soc. , 65 : 572
   Google Scholar
• Coyner , E. C. and Hillman , W. S. 1949 . J. Am. Chem. Soc. , 71 : 324
   Google Scholar
• Babler , J. H. and Sarussi , S. J. 1987 . J. Org. Chem. , 52 : 3462
   Web of Science ®Google Scholar
• Lennon , J. J. and Perkin , W.H. Jr. 1928 . J. Chem. Soc. , : 1513
   Google Scholar
• Gol'mov , V. P. and Malevannaya , Z. P. 1961 . J. Gen. Chem. U.S.S.R. , 31 : 613
   Google Scholar
• Bode , H. 1934 . Ber. , 67B : 332
   Google Scholar
• Fuson , R. C. and Kao , T. Y. 1929 . J. Am. Chem. Soc. , 51 : 1536
   Google Scholar
• Buchman , E. R. , Reims , A. O. , Skei , T. and Schlatter , M. J. 1942 . J. Am. Chem. Soc. , 64 : 2696
   Google Scholar
• Allinger , N. L. , Nakazaki , M. and Zalkow , V. 1959 . J. Am. Chem. Soc. , 81 : 4074
   Google Scholar
• Alberman , K. B. and Kipping , F. B. 1951 . J. Chem. Soc. , : 779
   Google Scholar
• Kipping , F. B. and Wren , J.J. 1957 . J. Chem. Soc. , : 3246
   Google Scholar
• Goldsworthy , L. J. 1924 . J. Chem. Soc. , 125 : 2012
   Google Scholar
• Raghu , S. U. S. Pat. . 4, 230, 860 .
   Google Scholar
• 1981 . Chem. Abs. , 94 : 102919 (American Cyanamid)
   Google Scholar
• 1976 . Chem. Abs. , 84 : 105082 Brevet Français 2 262 652 (Rhône Poulenc)
   Google Scholar
• Perrin , D. D. , Armarego , L. F. and Perrin , R. R. 1988 . Purification of Laboratory Chemicals, , 3rd Ed. , Oxford : Pergamon Press .
   Google Scholar
• The initial (60/40) cis/trans-diacid mixture was recrystallized three times from hot 12N HCl. The cis/trans ratio decreased to 45/55.
   Google Scholar
• Hengartner , U. , Valentine , D. Jr. , Johnson , K. K. , Larscheid , M. E. , Pigott , F. , Scheidl , F. , Scott , J. W. , Sun , R. C. , Townsend , J. M. and Williams , T. H. 1979 . J. Org. Chem. , 44 : 3741
   Web of Science ®Google Scholar