A New Route to 1,3-Dienes: TMSI Elimination of 2-Ene-1,4-diols

References

• Walborsky , H. M. and Wust , H. H. 1982 . J. Am. Chem. Soc. , 104 : 5807 For an application of this method to the vitamin D series, see Solladie, G. and Hutt, J., J. Org. Chem. 1987, 52, 3560
   Web of Science ®Google Scholar
• Kuhn , R. and Wallenfels , K. 1938 . Chem. Ber. , 71 : 1889
   Google Scholar
• Schmidt , A. H. 1981 . Aldrichimica Acta , 14 : 31 TMSI reviews
   Google Scholar
• Groutas , W. C. and Felder , D. 1980 . Synthesis , 11 : 861
   Google Scholar
• Olah , G. A. and Narang , S. C. 1982 . Tetrahedron , 38 : 2225 For the use of TMSI in elimination of 1,2-diols, see
   Web of Science ®Google Scholar
• Barva , N. C. , Sarma , J. C. , Sharma , R. P. and Barva , J. N. 1982 . Chem. and Ind. , : 956
   Google Scholar
• Barva , N. C. and Sharma , R. P. 1982 . Tetrahedron Lett. , 23 : 1365 For a related elimination with bridged dihydrofurans
   Google Scholar
• Jung , K. and Koreeda , M. 1989 . J. Org. Chem. , 54 : 5667
   Google Scholar
• Enediols which failed to give isolable products with TMSI include cis-2-butene-1,4-diol, trans-1-phenyl-2-butene-1,4-diol, cis-2,5-dimethyl-3-hexene-2,5-diol, and trans-4-(1-hydroxycyclohexyl)-2-methyl-3-butene-2–01
   Google Scholar
• Iyoda , M. , Nishioka , K. , Nose , M. , Tanaka , S. and Oda , M. 1984 . Chem. Lett. , : 131
   Google Scholar
• lyoda , M. , Tanaka , S. , Otani , H. , Nose , M. and Oda , M. 1988 . J. Am. Chem. Soc. , 110 : 8494
   Google Scholar
• Dupont , G. 1913 . Ann. Chim. , 30 ( 8 ) : 485
   Google Scholar
• Smith , B. , Ohlson , R. and Larson , G. 1963 . Acta Chem. Scand. , 17 : 436
   Google Scholar
• Rio , G. and Berthelot , J. 1969 . Bull. Soc. Chim. Fr. , : 1664
   Google Scholar
• Korach , M. , Nielsen , D. R. and Rideout , W. H. 1974 . Org. Synth., Coll. , 5 : 414
   Google Scholar
• Nugara , P. N. unpublished
   Google Scholar
• Craze , G.-A. and Watt , I. 1981 . J. Chem. Soc. Perkin Trans. II , : 175
   Google Scholar
• Tori , K. , Hata , Y. , Muncyuki , R. , Takano , Y. , Tsuji , T. and Tanida , H. 1964 . Can. J. Chem. , 42 : 926
   Google Scholar
• Crews , P. and Beard , J. 1973 . J. Org. Chem. , 38 : 522
   Google Scholar
• Kitahonoki , K. , Sakurawi , K. , Tori , K. and Ueyama , M. 1976 . Tetrahedron Lett. , : 263
   Google Scholar
• Campbell , W. P. and Harris , G. C. 1941 . J. Am. Chem. Soc. , 63 : 2721
   Google Scholar
• Hill , R. K. and Conley , R. T. 1960 . J. Am. Chem. Soc. , 8 ( 2 ) : 645
   Google Scholar