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2,3‐Bis(trimethylsilyloxy)‐1,3‐cyclohexadiene
Chapter

2,3‐Bis(trimethylsilyloxy)‐1,3‐cyclohexadiene

Abstract

[59733‐54‐9] C12H24O2Si2 (MW 256.54) [59733‐54‐9] C12H24O2Si2 (MW 256.54) InChI = 1S/C12H24O2Si2/c1‐15(2,3)13‐11‐9‐7‐8‐10‐12(11)14‐16(4,5)6/h9‐10H,7‐8H2,1‐6H3 InChIKey = GFBBOHLIHNZBMJ‐UHFFFAOYSA‐N (useful for Diels–Alder reactions giving highly functionalized [2.2.2] bicyclic systems) Physical Data: bp 102–103 °C/12 mmHg. Solubility: sol C6H6, Et2O. Preparative Method: by the sequential silylation of 1,2‐cyclohexanedione with a weak base and Trimethylsilyl Trifluoromethanesulfonate or under strongly basic conditions. Handling, Storage, and Precautions: silyl enol ethers are susceptible to hydrolysis under basic and especially acidic conditions or in the presence of fluoride ion and other silyl specific nucleophiles (e.g. DMSO, DMF). Precautions should therefore be adopted to protect such enol ethers from moisture.

Authors

Brook MA

Book title

Encyclopedia of Reagents for Organic Synthesis

Publisher

Wiley

Publication Date

January 1, 1995

DOI

10.1002/047084289x.rb218

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