On the Metalation-Silylation of 1,3,5-Trioxane

References

• Corey , E. J. and Seebach , D. 1965 . Angew. Chem. Int. Ed. Engl. , 4 : 1075 S,S-acetals:, Bürstinghaus, R., Seebach, D. Chem. Ber. 1977, 110, 841. (b) S,O-acetals: Fuji, K., Ueda, M., Sumi, K., Kajiwara, K., Fujita, E., Iwashita, T., Miura, I. J. Org. Chem., 1985, 50, 657, 663. (c) Application to acylsilane synthesis: Page, P.C.B., McKenzie, M.J., Klair, S.S., Rosenthal, S. in Rappoport, Z., Apeloig, Y., eds., “The Chemistry of Organosilicon Compounds” Vol. 2, Pt. 2, John Wiley & Sons, Chichester, 1998.
   Web of Science ®Google Scholar
• Shiner , S. S. , Tsunoda , T. , Goodman , B. A. , Ingham , S. , Lee , S. and Vorndam , P. E. 1989 . J. Am. Chem. Soc. , 111 : 1381
   Google Scholar
• Krizan , T. D. and Martin , J. C. 1983 . J. Am. Chem. Soc. , 105 : 6155 (b) Shimizu, N., Shibata, F., Tsuno, Y. Bull. Chem. Soc. Jpn., 1987, 60, 777. (c) Wright, S.W. Tetrahedron Lett., 1994, 35, 1841. (d) Yoon, K., Son, D.Y. J. Organometal. Chem., 1997, 545–546, 185.
   Google Scholar
• Snieckus , V. 1990 . Chem. Rev. , 90 : 879 Review
   Web of Science ®Google Scholar
• Soderquist , J. A. and Miranda , E. I. 1992 . J. Am. Chem. Soc. , 114 : 10078
   Web of Science ®Google Scholar
• The figures of Scheme 2 are not meant to stipulate the degree of association of lithium species or the exact timing of R′3SiX involvement
   Google Scholar
• Mai , K. and Patil , G. 1986 . J. Org. Chem. , 51 : 3545
   Google Scholar
• Omission of TMEDA afforded crude 1b of higher purity, but ultimate yields fell to 40–50%
   Google Scholar
• 1,3-Dioxolane was not derivatized with LiTMP-TMEDA-TESCN
   Google Scholar
• Becu , C. and Anteunis , M. J.O. 1987 . Bull. Soc. Chim. Belg. , 96 : 115
   Google Scholar
• Longer reaction times (41 h, -78° C) did not improve yields of 1b
   Google Scholar