Synthesis and kinetic cyclisation of quinine-derived oligomers

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 6013-6016

  Rowan, Stuart J ^a   Brady, Paul A ^a   Sanders, Jeremy K M ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

QUININE DERIVATIVE;

ARTICLE; CYCLIZATION; SYNTHESIS; THERMODYNAMICS;

EID: 0030581328     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01263-4     Document Type: Article

References (8)

1. 1. Brady, P.A.; Bonar-Law, R.P.; Rowan, S.J.; Suckling, C.J.; Sanders, J.K.M. Chem. Commun., 1996, 319.
2. 2. Rowan, S.J.; Brady, P.A.; Sanders, J.K.M. Angew. Chem., 1996, in press.
3. 3. Ercolani, G.; Mandolini, L.; Mencarelli, P.; Roelens, S. J. Am. Chem. Soc., 1993, 115, 3901.
4. 4. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
5. 5. Friedrich-Bochnitschek, S.; Waldmann, H.; Kunz, H. J. Org. Chem., 1989, 54, 751.
6. 6. Dalla Cort, A.; Ercolani, G.; Iamiceli, A.L.; Mandolini, L.; Mencarelli, P. J. Am. Chem. Soc., 1994, 116, 7081.
7. 1H NMR spectra is that relating to the 2' hydrogen. Cyclic trimer (1) δ = 8.76; Cyclic tetramer (2) δ = 8.73; Other cyclic oligomers δ = 8.70-8.65; Linear oligomers δ = 8.40 (monomer (6)), 8.53-8.59 (dimer(8)). 8.57-8.63 (trimer (12)); 8.64-8.68 (tetramer (15)).
8. 8. It follows therefore that the rate of ring opening for (1) is less than that for (2) and higher oligomers.