Evaluating the Baylis-Hillman reaction of cyclic enones using surfactants in water

Synlett

Volumn , Issue 19, 2005, Pages 2923-2926

  Porzelle, Achim ^a   Williams, Craig M ^a   Schwartz, Brett D ^a   Gentle, Ian R ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Aldehydes; Aqueous media; Baylis Hillman reaction; Cyclic enones; Green chemistry; Surfactant

Indexed keywords

CHEMICAL COMPOUND; ENONE DERIVATIVE; SURFACTANT; UNCLASSIFIED DRUG; WATER;

ARTICLE; BAYLIS HILLMAN REACTION; CONCENTRATION (PARAMETERS); MICELLE;

EID: 28844441269     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-921890     Document Type: Article

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15. Isolated yield 32%. Yield based on starting material recovery, 43%.
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18. 1H NMR data matched those in the literature. See:
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23. f = 0.33) to give 2 (39 mg, 85%) as a colorless liquid.
24. f = 0.33) to give 2 (30 mg, 65%) as a colorless liquid.
25. f = 0.36) to give 2-(hydroxymethyl)-4,4-dimethylcyclohex-2-enone (4c, 305 mg, 67%) as a colorless liquid.
26. We were unable to obtain the reported yield (99%, ref. 8).
27. f = 0.36) to give 2-[(4-nitrophenyl) (hydroxy)methyl]cyclohex-2-enone (6d, 500 mg, 68%) as a yellow syrup.
28. 2: 256.1463; found: 256.1458.
29. For a non-aqueous comparison, see: You, J.; Xu, J.; Verkade, J. G. Angew. Chem. Int. Ed. 2003, 42, 5054.