Intraannular functionalization of macrocyclic polyethers via organolithium intermediates

M Skowronska-Ptasinska, VMLJ Aarts…

Index: Skowronska-Ptasinska, Maria; Aarts, Veronika M. L. J.; Egberink, Richard J. M.; Eerden, Johan van; Harkema, Sybolt; Reinhoudt, David N. Journal of Organic Chemistry, 1988 , vol. 53, # 23 p. 5484 - 5491

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Citation Number: 19

Abstract

1, 3-Xylyl crown ethers substituted at the 2-position with an acidic (COOH, OH, S02H) or reactive (CHO) functional group can be synthesized from a common starting material by a generally applicable method that does not require the protection of these groups. 2-Bromo- 1, 3-xylyl crown ethers 1 react at-78" C with n-butyllithium to yield the corresponding 2-lithio- 1, 3-xylyl crown ethers 2 without extensive cleavage of the polyether ring. Subsequent ...