Applications of the baylis-hillman adducts in organic synthesis: A facile synthesis of [E]-α-cyanocinnamyl alcohols and [E]-α-cyanocinnamic aldehydes

Synlett

Volumn , Issue 10, 1999, Pages 1630-1632

  Basavaiah, Deevi ^a   Kumaragurubaran, Nagaswamy ^a   Padmaja, Kisari ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

And oxidation; Baylis Hillman reaction; Isomerization; E cyanocinnamic aldehydes; E cyanocinnamyl alcohols

Indexed keywords

CHROMIC ACID; CINNAMALDEHYDE; CINNAMYL ALCOHOL; NITRILE; PYRIDINIUM DERIVATIVE; SULFURIC ACID;

ARTICLE; CHEMICAL STRUCTURE; OXIDATION; POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032859209     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2893     Document Type: Article

References (25)

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21. 1H NMR spectrum of the crude product 2a shows the presence of = 15% unreacted starting material.
22. 9NO: C, 75.45; H, 5.70; N, 8.80 and found C, 75.31; H, 5.72; N, 8.87.
23. 13C NMR spectrum the allylic methylene carbon of the [E]-isomer appears at = δ 64.00 while that of the [Z]-isomer appears at = δ 57.00. In the case of molecule 2a, the allylic methylene carbon appears at δ 64.00. We have therefore assigned [E]-stereochemistry to 2a.
24. 1H NMR spectrum of the crude product shows the presence of =5-20% unreacted starting material.
25. 7NO: C, 76.42; H, 4.49; N, 8.91 and found C, 76.52; H, 4.48; N, 8.93.