Synthesis of E and Z Alkyl Tetrahydro-2-Pyrilidene and Tetrahydro-2-Furylidene Acetates

References

• N.S.E.R.C.C. and F.C.A.C. 1978–81 . predoctoral fellowships
   Google Scholar
• Deslongchamps , P. 1983 . “Stereoelectronic Effects in Organic Chemistry” , Organic Chemistry Series Edited by: Baldwin , J. E. Vol. 1 , 328 – 335 . Oxford, , England : Pergamon Press .
   Google Scholar
• Sauvé , G. , Schwartz , D. A. , Ruest , L. and Deslongchamps , B. Can. J. Chem. , In press
   Google Scholar
• The lithium enolate of ethyl and t-butyl acetate react with δ-valerolactone to yield the corresponding cyclic hemiketal, but the subsequent dehydration to give 4 was not reported.7
   Google Scholar
• Attempts to condense the sodium ester enolate of triethyl phosphonoacetate (Wadsworth-Emmons reaction)8 with δ-valero lactone were not successful.7
   Google Scholar
• δ-Valerolactone is known to react with the sodium enolate of diethyl cyanomethyl phosphonate to yield a 1:1 mixture of the coresponding Z and E conjugated enolether-nitrile (4, COOR[dbnd]CN) along with varying amount of non-conjugated endo cyclic isomer.7
   Google Scholar
• Duggan , A. J. , Adams , M. A. , Brynes , P. J. and Meinwald , J. 1976 . Tetrahedron Lett. , : 423
   Google Scholar
• Wadsworth , W. S. Jr. and Emmons , W. D. 1961 . J. Am. Chem. Soc. , 83 : 1733
   Web of Science ®Google Scholar
• Fessenden , R. J. and Fessenden , J. S. 1967 . J. Org. Chem. , 32 : 3535
   Web of Science ®Google Scholar
• Taguchi , H. , Shimoji , K. , Yamamoto , H. and Nozaki , H. 1974 . Bull. Chem. Soc. Jpn , 47 : 2529
   Web of Science ®Google Scholar
• Shimoji , K. , Taguchi , H. , Oshima , K. , Yamamoto , H. and Nozaki , H. 1974 . J. Am. Chem. Soc. , 96 : 1620
   Web of Science ®Google Scholar
• Ranthke , M. W. and Sullivan , D. F. 1973 . Synh. Commun. , 3 : 67
   Google Scholar
• Hartzell , S. L. , Sullivan , D. F. and Rathke , M. W. 1974 . Tetrahedron Lett. , : 1403
   Google Scholar
• For synthesis of alkyl α-(tetrahydro-2-furylidene)acetates
   Google Scholar
• Bryson , T. A. 1973 . J. Org. Chem. , 38 : 3428
   Google Scholar
• Krueger , S. A. and Bryson , T. A. 1974 . J. Org. Chem. , 39 : 3167
   Google Scholar
• Lhommet , G. , Eskenazi , C. and Maitte , P. 1974 . C. R. Hebd. Séances Acad. Sci. , 279 : 263 Ser. C
   Google Scholar
• Svendsen , A. and Boll , P. M. 1975 . Acta Chem. Scand. , 29 : 197 Ser. B
   Google Scholar
• Hartzell , S. L. and Rathke , M. W. 1976 . Tetrahedron Lett. , : 2757
   Google Scholar
• Deslongchamps , P. , Chěnevert , R. , Taillefer , R. J. , Moreau , C. and Saunders , J. K. 1975 . Can. J. Chem. , 53 : 1601
   Web of Science ®Google Scholar