Competing A1,3-strain and Ph:Ph diaxial repulsion in oximes and semicarbazones of N-nitroso-r-2,c-6-diphenylpiperidin-4-ones

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

Volumn 45, Issue 12, 2006, Pages 2720-2735

  Vijayalakshmi, R ^a,b,c   Muthukumar, M ^a   Ponnuswamy, S ^a,b,c   Jeyaraman, R ^a  

^a BHARATHIDASAN UNIVERSITY   (India)

^b QUEEN MARY S COLLEGE   (India)

^c GOVERNMENT ARTS COLLEGE   (India)

Author keywords

A1,3 strain; Configuration; Conformation; Epimerization; N nitroso r 2,c 6 diphenylpiperidin 4 ones; NMR spectra; Oximes; Semicarbazones; Semiempirical MO calculation; Twist boat

Indexed keywords

EID: 33846296572     PISSN: 03764699     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. (a) Chow Y L, Colon C J & Tam J N S, Can J Chem, 46, 1968, 2821;
2. (b) Ravindran T, Jeyaraman R, Murray R W & Singh M, J Org Chem, 56, 1990, 4833;
3. (c) Jeyaraman R, Thenmozhiyal J C, Murugadoss R & Muthukumar M, J Indian Chem Soc, 76, 1999, 527.
4. (a) Senthilkumar U P, Jeyaraman R, Murray R W & Singh M, J Org Chem, 57, 1992, 6006;
5. (b) Senthilkumar U P, Jeyaraman R & Bigler P, J Org Chem, 60, 1995, 7461;
6. (c) Ravindran T, Synthesis, Stereodynamics and Reactivity of N-nitroso-piperidines and N-nitrosoazabicyclo[3.3.1]nonanes, Ph.D. thesis, Bharathidasan University, India, 1993.
7. Johnson F & Malhotra S K, J Am Chem Soc, 87, 1965, 5492.
8. (a) Pandiarajan K, Mohan R T S & Ul Hasan M, Magn Reson Chem, 24, 1986, 312;
9. (b) Geneste P, Kamenka J M & Brevard C, Org Magn Reson, 10, 1977, 31.
10. Karabatsos G J & Hsi N, Tetrahedron 24, 1968, 3347.
11. Hawkes G E, Herwig K & Roberts J D, J Org Chem, 39, 1974, 1017.
12. Slessor K N & Tracey A S, Can J Chem, 49, 1971, 2874.
13. (a) Geneste P, Kamenka J M, Hugon I & Graffin P, J Org Chem, 41, 1976, 3637;
14. (b) Roques P R, Declercq J P, Germain G, Graffin P, Kamenka J M & Geneste P, Acta Crystallogr, 837, 1981, 712.
15. (a) Haller R & Ziriakus W, Arch Pharm, 305, 1972, 541;
16. (b) Haller R & Ziriakus W, Tetrahedron 28, 1972, 2863;
17. (c) Haller R & Ziriakus W, Arch Pharm, 28, 1972, 741.
18. Goren Z & Biali S E, J Am Chem Soc, 112, 1990, 893.
19. Sukumar N, Ponnusamy M N, Vijayalakshmi R & Jeyaraman R, Z Kristallogr, 209, 1994, 823.
20. (a) Dewar M J S, Zoebisch E G, Healy E F & Stewart J J P, J Am Chem Soc, 107, 1985, 3902;
21. (b) Stewart J J P, J Comput Aided Mol Des, 4, 1990, 1.
22. Vijayalakshmi R, Studies on the Stereochemistry and Reactions of Piperidines having Heteroconjugate Groups, Ph.D. thesis, Bharathidasan University, India, 1994.