A New Synthesis of 3-Chloro Butenolides via Rearrangement of 3,3-Dichloro Beta Lactones

References

• Black , T. H. , DuBay , W. J. and Tully , P. S. 1988 . J. Org. Chem. , 53 : 5922
   Web of Science ®Google Scholar
• Black , T. H. , Hall , J. A. and Sheu , R. G. 1988 . J. Org. Chem. , 53 : 2371
   Web of Science ®Google Scholar
• Black , T. H. , Eisenbeis , S. A. , McDermott , T. S. and Maluleka , S. L. 1990 . Tetrahedron , 46 : 2307
   Google Scholar
• Mulzer , J. and Bruntrup , G. 1979 . Angew. Chem., Int. Ed. Engl. , 18 : 793 This type of rearrangement was originally thought to be an example of an organic dyotropic process, however, subsequent work is more consistent with a carbocation intermediate.
   Web of Science ®Google Scholar
• Brady , W. T. and Patel , A. D. 1972 . Synthesis , 565
   Google Scholar
• Coutrot , P. and ElGadi , A. 1984 . Synthesis , 115
   Google Scholar
• Rosini , G. , Ballini , R. and Zarotti , R. 1983 . Tetrahedron , 39 : 1085
   Web of Science ®Google Scholar
• This method was far superior to generation of dichloroketene via amine-mediated dehydrochlorination of dichloroacetyl chloride
   Google Scholar
• FT-IR (neat): 2982.2, 2941.2, 1167.8, 1651.2, 1463.2, 1383.8, 1323.2, 1172.6, 1108.4, 1026.0 cm−1; 1H-NMR (500 MHz, CDClg): γ = 4.97 (q, J=6.7 Hz, 1H), 2.53 (sextet, J = 7.5 Hz, 1H), 2.29 (sextet, J = 7.3 Hz, 1H), 1.39 (d, J=6.7 Hz, 3H), 1.11 (t, J=7.6 Hz, 3H); 13C-NMR (500 MHz, CDCl3): A = 167.97, 165.30, 118.61, 78.73, 20.08, 18.16, 11.14 ppm. TLC (CH2C12): Rf = 0.51.;
   Google Scholar
• Prepared via the reaction of 1,2-dibromoethane with magnesium
   Google Scholar
• Gray , M. J. , Hartshorn , M. P. , Penfold , B. R. and Vaughan , J. 1984 . Aust. J. Chem. , 37 : 55
   Google Scholar
• Heubach , G. 1982 . Liebigs Ann. Chem. , : 1017
   Google Scholar
• Farina , F. , Martin , M. V. , Sanchez , F. , Maestro , M. C. and Martin , M. R. 1983 . Heterocycles , 20 : 1761
   Google Scholar
• Takeda , K. , Kubo , H. , Koizumi , T. and Yoshii , E. 1982 . Tetrahedron Lett. , 23 : 3175
   Google Scholar
• Meul , T. , Miller , R. and Tenud , L. 1987 . Chimia , 41 : 73
   Google Scholar
• Kosugi , Y. , Hamaguchi , F. , Nagasaka , T. and Ohki , S. 1982 . Heterocycles , 19 : 1013
   Google Scholar
• Farina , F. , Martin , M. V. and Sanchez , F. 1986 . Heterocycles , 24 : 2587
   Google Scholar