Molecular orbital studies on the Wagner-Meerwein migration in some acyclic pinacol-pinacolone rearrangements

Journal of Chemical Sciences

Volumn 116, Issue 2, 2004, Pages 83-91

  Pachuau, Zodinpuia ^a   Lyngdoh, R H Duncan ^a  

^a NORTH EASTERN HILL UNIVERSITY   (India)

Author keywords

Hammond's postulate; Pinacol pinacolone rearrangement; PM3 SCF MO method; Relative migratory aptitude; Transition state geometry; Wagner Meerwein migration

Indexed keywords

ACTIVATION ENERGY; ALCOHOLS; CARBON; DEHYDRATION; HYDRIDES; ISOMERS; KETONES; POSITIVE IONS; REACTION KINETICS; STEREOCHEMISTRY;

HAMMOND'S POSTULATE; PINACOL-PINACOLONE REARRANGEMENT; PM3 SCF-MO METHOD; RELATIVE MIGRATORY APTITUDE; TRANSITION STATE GEOMETRY; WAGNER-MEERWEIN MIGRATION;

MOLECULAR STRUCTURE;

EID: 2342443183     PISSN: 02534134     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02708200     Document Type: Article

References (29)

1. Olah G A and Schleyer P v R 1969 Carbonium ions (New York, London, Sydney, Toronto: Wiley-Interscience) vol. 2; Olah G A and Schleyer P v R 1971 Carbonium ions (New York, London, Sydney, Toronto: Wiley-Interscience) vol. 3; Creary X 1991 Chem. Rev. 91 1625
2. Olah G A and Schleyer P v R 1969 Carbonium ions (New York, London, Sydney, Toronto: Wiley-Interscience) vol. 2; Olah G A and Schleyer P v R 1971 Carbonium ions (New York, London, Sydney, Toronto: Wiley-Interscience) vol. 3; Creary X 1991 Chem. Rev. 91 1625
3. Olah G A and Schleyer P v R 1969 Carbonium ions (New York, London, Sydney, Toronto: Wiley-Interscience) vol. 2; Olah G A and Schleyer P v R 1971 Carbonium ions (New York, London, Sydney, Toronto: Wiley-Interscience) vol. 3; Creary X 1991 Chem. Rev. 91 1625
4. Vogel P 1985 Organic chemistry: Studies in organic chemistry 21 (New York: Elsevier Science) ch. 10; Saunders M and Jiminez-Vazquez H A 1991 Chem. Rev. 91 375
5. Vogel P 1985 Organic chemistry: Studies in organic chemistry 21 (New York: Elsevier Science) ch. 10; Saunders M and Jiminez-Vazquez H A 1991 Chem. Rev. 91 375
6. Pine S H 1987 Organic chemistry 5th edn (Singapore: McGraw-Hill) p. 973
7. Sykes P 1986 A guide book to mechanism in organic chemistry 6th edn (New Delhi: Orient Longman) p. 111
8. Fittig W 1859 Annalen 110 23; Fittig W 1860 Annalen 114 54
9. Fittig W 1859 Annalen 110 23; Fittig W 1860 Annalen 114 54
10. Collins C J 1960 Q. Rev. 375
11. Cecchi P, Cipollini R, Pizzabiocca A, Renzi G and Speranza M 1988 Tetrahedron 44 4847
12. Suzuki K, Ohkuma T, Miyazawa M and Tsichihashi G 1986 Tetrahedron Lett. 27 373
13. Suzuki K, Katayama E and Tsuchihashi G 1984 Tetrahedron Lett. 25 1817
14. Suzuki K, Katayamma E and Tsuchihashi G 1983 Tetrahedron Lett. 24 4997
15. Stiles M and Meyer R P 1959 J. Am. Chem. Soc. 81 1499
16. Shono T, Fujita K, Kumai S, Watanabe T and Nishiguchi I 1972 Tetrahedron Lett. 31 3249
17. Pilkington J W and Waring A J 1973 Tetrahedron Lett. 44 4345
18. Tsuchihashi G, Tomooka K and Suzuki K 1984 Tetrahedron Lett. 25 4253
19. Shine H J 1967 Aromatic rearrangements (Amsterdam, London, New York: Elsevier) eh. 1
20. Collins C J 1955 J. Am. Chem. Soc. 77 5517
21. Carlin R B and Shivaramakrishnan K P 1970 J. Org. Chem. 35 2368
22. Mayo P D 1980 Rearrangement in ground and excited states (New York: Academic Press) p. 35
23. Harnmond G S 1955 J. Am. Chem. Soc. 77 334
24. Stewart J J P 1989 J. Comput. Chem. 10 209
25. Stewart J J P 1983 QCPE Bull. 3 43
26. Shano D F J 1985 Opt. Theory Appl. 46 87; Stewart J J P 1990 Frank J Seiler Research Laboratory, United States Air Force Academy, CO 80840
27. Shano D F J 1985 Opt. Theory Appl. 46 87; Stewart J J P 1990 Frank J Seiler Research Laboratory, United States Air Force Academy, CO 80840
28. Maquestiau A, Flammang R, Flammang-Barbieux M and Mispreuve H 1980 Tetrahedron 36 1994
29. Young-Sook P H 1988 Bull. Korean Chem. Soc. 10 151