Synthesis, Structure, and Stereodynamics of an N, N??Chiral “Proton Sponge”

…, P Jonathan, GC Lloyd??Jones…

Index: Charmant, Jonathan P. H.; Lloyd-Jones, Guy C.; Peakman, Torren M.; Woodward, Robert L. European Journal of Organic Chemistry, 1999 , # 10 p. 2501 - 2510

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Citation Number: 15

Abstract

Abstract 1, 8-Bis (N-benzyl-N-methylamino) naphthalene (2) and its hydrogen iodide salt [2H]+[I]–were synthesised from 1, 8-diaminonaphthalene. The thermodynamic diastereomer ratios of (2) and [2H]+ in [D 7] DMF are 73.4: 26.6 and 89.7: 10.3 respectively at 293 K. The solid state structures of the major dl-(RNRNSNSN) diastereomers were determined by single crystal X-ray diffraction. The minor diastereomers were shown to be the meso-( ...