Regio- and stereochemistry of Michael addition of methanol to Thiele's ester

Journal of Physical Organic Chemistry

Volumn 17, Issue 3, 2004, Pages 174-179

  Minter, David E ^a   Smith, William B ^a   Marchand, Alan P ^b   Etukala, Jagan Reddy ^b   Sivappa, Rasapalli ^b  

^a TEXAS CHRISTIAN UNIVERSITY   (United States)

^b UNIVERSITY OF NORTH TEXAS   (United States)

Author keywords

Michael reactions; NMR; Polycyclic aliphatic compounds; Theoretical studies

Indexed keywords

ADDITION REACTIONS; CALCULATIONS; CHEMICAL BONDS; ESTERIFICATION; ESTERS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE TRANSITIONS; PROBABILITY DENSITY FUNCTION; QUANTUM THEORY; STEREOCHEMISTRY; THERMODYNAMICS;

MICHAEL ADDITION; POLYCYCLIC ALIPHATIC COMPOUND;

METHANOL;

EID: 1542500609     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.710     Document Type: Article

References (30)

1. (a) Thiele J. Chem. Ber. 1900; 33: 666
2. (b) Thiele J. Chem. Ber. 1901; 34: 68.
3. Dunn GL, Donohue JK. Tetrahedron Lett. 1968; 3485-3487.
4. Minter DE, Marchand AP, Lu S-P. Magn. Reson. Chem. 1990; 28: 623-627, and references cited therein.
5. (a) Marchand AP, Zhao D, Ngooi T-K, Vidyasagar V, Watson WH, Kashyap R. Tetrahedron 1993; 49: 2613-2620
6. (b) Marchand AP, Namboothiri INN., Lewis SB, Watson WH, Bodige SG. Tetrahedron 1998; 54: 12691-12698.
7. Franklin WE, Mack CH, Rowland SP. J. Org. Chem. 1968; 33: 626-632.
8. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr., Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Latham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C., Head-Gordon M, Replogle ES, Pople JA. Gaussian 98, Revision A.4. Gaussian: Pittsburgh, PA, 1998.
9. (a) Barfield M, Smith WB. J. Am. Chem. Soc. 1992; 114: 1574-1581
10. (b) Smith WB Magn. Reson. Chem. 1999; 37: 103-106
11. (c) Barfield M, Fagerness P. J. Am. Chem. Soc., 1997; 119: 8699.
12. (a) Peng C, Schlegel HB. Israel J. Chem. 1993; 33: 449-454
13. (b) Peng C, Ayala PY, Schlegel HB, Frisch MJ. J. Comput. Chem. 1996; 17: 49-56.12.
14. (a) van Duijneveldt FB, Van Duijneveldt-van de Rejdt JGCM, Van Lenthe JH. Chem. Rev. 1994; 94: 1873-1885
15. (b) Chalasinski G, Szczesniak MM. Chem. Rev. 2000; 100: 4227-4252.
16. Miertus S, Tomasi J. J. Phys. Chem. 1987; 99: 3616.
17. Grutzner JB, Jautelat M, Dence JB, Smith RA, Roberts JD. J. Am. Chem. Soc. 1970; 92: 7107-7120.
18. (a) Meinwald J, Lewis A. J. Am. Chem. Soc. 1961; 83: 2769-2770
19. (b) Marchand AP, Marchand NW, Segre AL. Tetrahedron Lett. 1969; 5207-5210
20. (c) Marchand AP. Stereochemical Applications of NMR Studies in Rigid Bicyclic Ring Systems. Verlag Chemie International: Deerfield Beach, FL, 1982, and references cited therein.
21. Wolinski K, Hinton JF, Pulay P. J. Am. Chem. Soc. 1990; 112: 8251-8260.
22. Forsyth DA, Sebag AB. J. Am. Chem. Soc. 1997; 119: 9483-9494.
23. Marchand AP, Namboothiri INN, Lewis SB, Watson WH, Krawiec M. Tetrahedron 1998; 54: 12691-12698.
24. Moffett RB. Org. Synth., Coll. 1963; 4: 238-241.
25. Peters D. J. Chem. Soc. 1959; 1761-1765.
26. (a) Bax A, Griffey RH, Hawkins BL. J. Magn. Reson. 1983; 55: 301-315
27. (b) Bax A, Subramanian S. J. Magn. Reson. 1986; 67: 565-569.
28. (a) Bax A, Summers MF. J. Am. Chem. Soc. 1986; 108: 2093-2094
29. (b) Bermel W, Wagner K, Griesinger C. J. Magn. Reson. 1989; 83: 223-232
30. (c) Kessler H, Schmieder P, Kock M, Kurz M. J. Magn. Reson. 1990; 88: 615-618.