84247-81-4

Basic information

• Product Name: (1E,3Z)-1-trimethylsilyl-4-phenyl-1,3-butadiene
• Synonyms: (1E,3Z)-1-trimethylsilyl-4-phenyl-1,3-butadiene
• CAS NO: 84247-81-4
• Molecular Weight: 202.371
• Mol File: 84247-81-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (1E,3Z)-1-trimethylsilyl-4-phenyl-1,3-butadiene(CAS DataBase Reference)
• NIST Chemistry Reference: (1E,3Z)-1-trimethylsilyl-4-phenyl-1,3-butadiene(84247-81-4)
• EPA Substance Registry System: (1E,3Z)-1-trimethylsilyl-4-phenyl-1,3-butadiene(84247-81-4)

Safety Data

• Hazardous Substances Data: 84247-81-4(Hazardous Substances Data)

Upstream product

• 17891-78-0 1,3-bis(trimethylsilyl)propene 
• 100-52-7 benzaldehyde 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 754-05-2 ethenyltrimethylsilane 
• 42201-74-1 <β-(Trimethylsilyl)vinyl>magnesium bromide 
• 13984-49-1 (phenylethynyl)zinc chloride 
• 41309-43-7 (2-bromovinyl)trimethylsilane 
• 17891-78-0 2,2,6,6-tetramethyl-2,6-disila-3-heptene 
• 92509-53-0 (E)-trimethyl(4-phenylbut-1-en-3-yn-1-yl)silane 
• 61518-50-1 1,3-bis(trimethylsilyl)prop-1-enyl-lithium 
• 120764-58-1 (1E,3Z)-4-phenylthio-1-trimethylsilyl-1,3-butadiene 
• 536-74-3 phenylacetylene 

Relevant articles and documents

Aza-peterson olefinations: Rapid synthesis of (E)-alkenes

An aza-Peterson olefination methodology to access 1,3-dienes and stilbene derivatives from the corresponding allyl- or benzyltrimethylsilane is described. Silanes can be deprotonated using Schlosser's base and added to N -phenyl imines or ketones to directly give the desired products in high yields.

PALLADIUM-CATALYZED DIASTEREOSELECTIVE SYNTHESES OF (E)-1-TRIMETHYLSILYL-2-ALKENES, (E)-1-TRIMETHYLSILYL-1-ALKEN-3-YNES, (1E,5E)-1-TRIMETHYLSILYL-1,5-ALKADIEN-3-YNES, (1E,3Z)- AND (1E,3E)-1-TRIMETHYLSILYL-1,3-ALKADIENES

On the basis of our observation that (E)-1-bromo-1-alkenes undergo preferentially stereospecific Pd-catalyzed cross-couplings with a variety of organometallics, in the presence of the corresponding (Z)-stereoisomers, efficient and convenient diastereoselective procedures have been developed to prepare nearly stereoisomerically pure (E)-1-trimethylsilyl-2-alkenes (4), (E)-1-trimethylsilyl-1-alken-3-ynes (5), (1E,5E)-1-trimethylsilyl-1,5-alkadien-3-ynes (6), and (1E,3E)-1-trimethylsilyl-1,3-alkadienes (8) from stereoisomeric mixtures of alkenyl bromides.Compounds 5 have been stereoselectively converted into (1E,3Z)-1-trimethylsilyl-1,3-dienes (7) by selective hydrometallations, followed by hydrolysis.Some synthetic applications of compounds 5-8 have been also examined.

STEREOSPECIFIC SYNTHESIS OF (1E,3Z)-AND (1E,3E)-1-TRIMETHYLSILYL-1,3-DIENES BY MEANS OF SEQUENTIAL CROSS-COUPLING REACTIONS

A new synthesis of stereodefined 1-trimethylsilyl-1,3-dienes is described.The method is based on two sequential coupling reactions between Grignard reagents and the readily available (Z)-or (E)-1-bromo-2-phenylthioethene, in the presence of transition met