Reaction of carbon monoxide with N-Lithioketimines derived by the addition of alkyllithium to ortho-substituted benzonitriles. Diverse courses of cyclization via carbonyl anions

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 9027-9030

  Kai, Hidetomo ^a   Yamauchi, Masakazu ^a   Murai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; BENZONITRILE; CARBON MONOXIDE; CARBONYL DERIVATIVE;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030779434     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10412-9     Document Type: Article

References (19)

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12. Smith, K.; Pritchard, G. J. Angew. Chem., Int. Ed. Engl. 1990, 29, 282.
13. 21NO: 231.1624, found 231.1640.
14. We cannot rule out lithioxycarbene 9' as an alternative intermediate which could insert into the benzyl C-H bond to afford 11. (a) A lithioxycarbene intermediate has been proposed in the reaction of lithium amide with carbon monoxide, see: Viruela-Martin, P.; Viruela-Martin, R.; Tomás, F.; Nudelmann, N. S. J. Am. Chem. Soc. 1994, 116, 10110.
15. (b) The siloxycarbene intermediate, which is the silicon analogue of lithioxycarbene, was reported to undergo intramolecular C-H bond insertion, see: Bassindale, A. R.; Brook, A. G.; Harris, J. J. Organomet. Chem. 1975, 90, C6. Ando, W.; Sekiguchi, A. J. Organomet. Chem. 1977, 133, 219. matrix presented
16. (b) The siloxycarbene intermediate, which is the silicon analogue of lithioxycarbene, was reported to undergo intramolecular C-H bond insertion, see: Bassindale, A. R.; Brook, A. G.; Harris, J. J. Organomet. Chem. 1975, 90, C6. Ando, W.; Sekiguchi, A. J. Organomet. Chem. 1977, 133, 219. matrix presented
17. The compounds were characterized by NMR, IR, mass spectral data and elemental analysis or high resolution mass spectra.
18. The described N-lithioketimines were generally prepared in the range of 80-95% yield as confirmed by quenching with MeI.
19. A similar t-Bu group migration was observed, see ref 3c and 4.