An efficient synthesis of N-unsubstituted imines as organoborane adducts stable at room temperature: New promising intermediates for synthesis [3]

Journal of the American Chemical Society

Volumn 122, Issue 17, 2000, Pages 4217-4218

  Chen, Guang Ming ^a   Brown, Herbert C ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; IMINE;

CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; LETTER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 0034600321     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993965v     Document Type: Letter

References (21)

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18. In fact, 1 can be methanolyzed instantly and completely in the presence of only 5 mol % of 3 at -78°C. The free aldimine produced, as reported previously (ref 10), is not stable even for a short period. For characterization of the E- and Z-isomer of aldimines, see ref 8.
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20. The geometry of 26 was determined by X-ray crystallography as E. The variable-temperature NMR technique reveals only one isomer. The geometry of other ketimines was then determined based on the analogy.
21. 2, followed by the addition of Grignard reagent, provides the product 3,3-dimethyl-4-phenylazetidin-2-one in 94% isolated yield.