Preparation of 2-iodo allylic alcohols from 2-butyn-1,4-diol.
The conversion of 2-butyn-1,4-diol to (Z)-2,4-diiodobut-2-en-1-ol proceeded efficiently using in situ generated trimethylsilyl iodide. Coupling with Grignard reagents and other nucleophiles delivered (2Z)-2-iodo allylic alcohols. The geometry of the products was established by nOe.
Taber
Douglass F
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
Sikkander
M Inthikhab
MI
Berry
James F
JF
Frankowski
Kevin J
KJ
D002072:Butylene Glycols / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D020005:Propanols / Q000138:chemical synthesis* / Q000737:chemistry; D013055:Spectrophotometry, Infrared
D002072:Butylene Glycols; D020005:Propanols; C006463:allyl alcohol; C009733:2-butyne-1,4-diol