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.

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Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2008-02, Vol.73 (4), p.1605-1607
Hauptverfasser:	Taber, Douglass F, Sikkander, M. Inthikhab, Berry, James F, Frankowski, Kevin J
Format:	Artikel
Sprache:	eng
Schlagworte:	Butylene Glycols - chemistry Chemistry Exact sciences and technology Magnetic Resonance Spectroscopy Noncondensed benzenic compounds Organic chemistry Preparations and properties Propanols - chemical synthesis Propanols - chemistry Spectrophotometry, Infrared
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Beschreibung
Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo7021197