References
- Andersen , N. H. , Uh , H. S. , Smith , S. E. and Wuts , P. G. M. 1972 . J. Chem. Soc., Chem. Commun. , : 956 For six-membered ring formation, see: a)
- McCurry , P. M. and Singh , R. K. 1973 . Tetrahedron Lett. , : 3325
- Marshall , J. A. and Andersen , N. H. 1967 . Tetrahedron Lett. , : 1219 For seven-membered rings: a)
- Marshall , J. A. , Andersen , N. H. and Johnson , P. C. 1967 . J. Am. Chem. Soc. , 89 : 27 – 8 .
- Marshall , J. A. , Andersen , N. H. and Schlicher , J. W. 1970 . J. Org. Chem. , 35 : 858
- Andersen , N. H. and Golec , F. A. Jr. 1977 . Tetrahedron Lett. , : 3733
- Schulte-Elte , K. H. and Ohloff , G. 1967 . Helv. Chim. Acta , 50 : 153
- Schwartz , M. A. , Crowell , J. D. and Musser , J. H. 1972 . J. Am. Chem. Soc. , 94 : 4361
- Marshall , J. A. and Wuts , P. G. M. 1977 . J. Org. Chem. , 42 : 1794
- Bryon Gill , G. and Wallace , B. 1977 . J. Chem. Soc., Chem. Commun. , 380 : 382 For a recent “rediscovery” of this reaction, see
- Uh , H. S. and Wuts , P. G. M. Unpublished studies with. These failures are further evidence for the concerted mechanism, revealing the strain associated with meta-fusing a six-centered T. S. onto the small ring
- Andersen , N. H. , Bottino , B. J. and Smith , S. E. 1972 . J. Chem. Soc., Chem. Commun. , : 1193 The general methods for our LIS studies and structure-LIS correlations have been given previously: see also - N. H. Andersen, C.-L. W. Tseng, A. Moore, and Y. Ohta, Tetrahedron, 34, 47 (1978), particularly note #23
- Eliel , E. L. , Allinger , N. L. , Angyal , S. J. and Morrison , G. A. Vol. 1965 , 228 New York, N. Y. : Interscience Publishers (John Wiley and Sons) . “Conformational Analysis”
- Foote , C. S. and Woodward , R. B. 1964 . Tetrahedron , 20 : 687 Hydrindan-4-one equilibration would provide closer analogy including the sp2 center, but we were unable to loCate firm data concerning the equilibrium ratio of cis and trans-hydrindan-4-one, a suggested value is 3:1 cis:trans
- Gaoni , Y. and Wenkert , E. 1966 . J. Org. Chem. , 31 : 3809 see also A. W. Allen, R. P. A. Sneeden and J. Colvin, J. Chem. Soc., 556 (1958)
- Halsall , T. G. and Thomas , D. B. 1956 . J. Chem. Soc. , : 2438
- Edwards , J. H. and McQuillan , F. J. 1977 . J. Chem. Soc. Chem. Commun. , : 838
- See the accompanying article
- Corey , E. J. and Boger , D. L. 1978 . Tetrahedron Lett. , : 9 Successful conjugate additions of R2CuLi to α,[btilde]-unsaturated aldehydes are very rare. This has also been noted by others and alternative formyl equivalents have been developed: and ref. cited therein