rac-2-Cyano-2-( p-tolyl)sparteine and its perchlorate salt

2-Cyano-2-( p-tolyl)sparteine (VI) and its monoperchlorate (VI-Hþ) have been obtained and characterized by IR and NMR spectroscopy as well as by X-ray diffraction analysis. Conformational–configurational change of the C/D ring system, upon protonation, from trans boat/chair to cis chair/chair, observed in the investigated doubly substituted derivative, follows the same pattern as in sparteine. However, while in the crystal of sparteine monoperchlorate the acidic H-atom bonds to N-1, being part of trans-quinolizidine system, in all three crystallographic independent molecules of 2-cyano-2-( p-tolyl)sparteine it bonds to N-16 nitrogen atom which belongs to cis-quinolizidine system. q 2003 Elsevier B.V. All rights reserved