C-C coupling reaction of 1,5-dibromo-2,6-dihydroxynaphthalene with alakli 2-naphthoxide. Opposite effects of counterion coordination and hydrogen bonding on stereoselectivity in the formation of cis- and trans-1,1':5',1''-ternaphthyls

Tetrahedron

Volumn 52, Issue 33, 1996, Pages 11013-11024

  Bělohradský, Martin ^a   Buděšínský, Miloš ^a   Günterová, Jana ^a   Hodačová, Jana ^a   Holý, Petr ^a   Zâvada, Jiří ^a   Cisařová, Ivana ^b   Podlaha, Jaroslav ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHYL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE; THERMODYNAMICS;

EID: 0030581412     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00619-9     Document Type: Article

References (7)

1. 1. Bělohradský, M.; Buděšínský, M.; Günterová, J.; Hodačová, J.; Holý, P.; Závada, J.; Císařová, I.; Podlaha, J. J. Org. Chem. 1996, 61, 1205-1210.
2. 2. Only one enantiomer of cis-5 is shown in the Scheme 2.
3. 3. Bělohradský, M.; Holý, P.; Závada, J. J. Chem. Soc. Perkin Trans. 2 1995, 1853-1856.
4. 4. The percentage of ether 6 was significantly higher in the runs which had not been deaerated by flushing with argon prior to the reaction.
5. 5. Holy, P.; Bělohradský, M.; Závada, J. Synth. Commun. 1996, in press.
6. 6. Sheldrick, G. M. Acta Crystalogr., Sect. A, 1990, A46, 467-482.
7. 7. G. M. Sheldrick, SHELXL-93, Program for Crystal Structure Refinement from Diffraction Data, University of Göttingen, 1993.