Amino-, Alkoxy-, and Alkylthio-Isocyanates and -Isothiocyanates, RX-NCY, their Isomers RX-YCN and RX-CNY, and their Rearrangements

Wentrup, Curt, Finnerty, Justin J. and Koch, Rainer (2011) Amino-, Alkoxy-, and Alkylthio-Isocyanates and -Isothiocyanates, RX-NCY, their Isomers RX-YCN and RX-CNY, and their Rearrangements. Current Organic Chemistry, 15 11: 1745-1759. doi:10.2174/138527211795656624

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Author Wentrup, Curt
Finnerty, Justin J.
Koch, Rainer
Title Amino-, Alkoxy-, and Alkylthio-Isocyanates and -Isothiocyanates, RX-NCY, their Isomers RX-YCN and RX-CNY, and their Rearrangements
Journal name Current Organic Chemistry   Check publisher's open access policy
ISSN 1385-2728
1875-5348
Publication date 2011-06
Sub-type Article (original research)
DOI 10.2174/138527211795656624
Volume 15
Issue 11
Start page 1745
End page 1759
Total pages 15
Place of publication Bussum, Netherlands
Publisher Bentham Science Publishers
Collection year 2012
Language eng
Abstract Hetero-substituted isocyanates and isothiocyanates RX-NCY (X = R2N, RO, or RS; Y = O or S) and the isomeric cyanates RX-OCN, thiocyanates RX-SCN, nitrile oxides RX-CNO, and nitrile sulfides RX-CNS are highly reactive compounds, often transient at room temperature. The chemistry of these compounds is reviewed. A number of rearrangement reactions is described, particularly [3,3]- sigmatropic shifts, e.g. PhX-NCY → o-HX-C6H4-YCN (X = NR, O, S; Y = O, S); and retro-ene type reactions, RCH2X-NCY → RCH=X + HYCN (X = NR, O, S; Y = O, S). In addition, potential 1,4-shifts of substituent groups of the type R-Y-CNX → R-X-N=C=Y; 1,3- shifts R-C(=Y)-N=X → R-X-N=C=Y; and 1,2-shifts R-C(=Y)-N=X → R-Y-CNX were identified computationally.
Keyword Isocyanates
Isothiocyanates
Cyanates
Thiocyanates
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2012 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Fri, 02 Mar 2012, 09:38:50 EST by Lucy O'Brien on behalf of School of Chemistry & Molecular Biosciences