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Synthesis and characterization of a novel pentacyclic C16 diketone and derivatives

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Abstract

The syntheses and crystal structures of pentacyclo[9.4.1.05,14.07,13.012,15]hexadecane-3,9-dione (2), a novel C16 diketone with potential inclusion ability, and the products of the reaction of2 withn-butyllithium andmeso-erythritol (i.e.,meso-1,2,3,4-butanetetrol) are described. Crystal data:2·H2O, orthorhombic,Pmmn,a=10.7385(8),b=9.0188(6),c=6.8411(4)Å,V=662.55(7)Å3, andR=0.039 (379 reflections);3 (product from reaction withn-butyllithium), triclinic,P¯1,a=8.7192(7),b=10.9351(8),c=12.1842(8)Å,α=68.933(5),β=75.850(6), γ=80.309(6)°,V=1047.0(1)Å3, andR=0.081 (1811 reflections);4 (product from reaction with erythritol), triclinic,P¯1,a=7.7224(8),b=10.1976(8),c=10.7021(9)Å,α=85.405(7),β=85.766(8), γ=76.056(7)°,V=814.0(1)Å3, andR=0.052 (1471 reflections).

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Bott, S.G., Marchand, A.P. & Raja Gopal, D. Synthesis and characterization of a novel pentacyclic C16 diketone and derivatives. Journal of Crystallographic and Spectroscopic Research 23, 849–855 (1993). https://doi.org/10.1007/BF01195731

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