Brassard's Diene
Title: Brassard's Diene
CAS Registry Number: 90857-62-8 (E-form); 74272-66-5 (stereo unspecified)
CAS Name: [[(1E)-1,3-Dimethoxy-1,3-butadienyl]oxy]trimethylsilane
Additional Names: 1,3-dimethoxy-1-trimethylsiloxy-1,3-butadiene
Molecular Formula: C9H18O3Si
Molecular Weight: 202.32
Percent Composition: C 53.43%, H 8.97%, O 23.72%, Si 13.88%
Literature References: Highly reactive nucleophilic silyloxydiene; cf. Danishefsky's diene. Prepn: J. Savard, P. Brassard, Tetrahedron Lett. 20, 4911 (1979); eidem, Tetrahedron 40, 3455 (1984). Synthetic applications: M. M. Midland, R. W. Koops, J. Org. Chem. 55, 5058 (1990); T. Ito et al., Tetrahedron Lett. 34, 6583 (1993); Q. Fan et al., Eur. J. Org. Chem. 2005, 3542; of polymer-supported derivatives: C. Pierres et al., Tetrahedron Lett. 44, 3645 (2003).
Properties: Oil. bp0.5 54°. bp0.8 57-62°.
Boiling point: bp0.5 54°; bp0.8 57-62°
Use: Electron-rich diene in hetero Diels-Alder reactions.

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