87673-47-0

Upstream product

• 1066-45-1 trimethyltin(IV)chloride 
• 917-54-4 methyllithium 
• 1191-15-7 diisobutylaluminium hydride 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 120-94-5 1-Methylpyrrolidine 
• 75-77-4 chloro-trimethyl-silane 
• 97537-75-2 (1-trimethylstannyl-2-phenyl)vinyllithium 
• 78338-47-3 C₆H₅CHC(Sn(CH₃)3)2 
• 16029-98-4 trimethylsilyl iodide 

Downstream Products

• 136366-02-4 (E)-1-benzoyl-2-phenylethenyltrimethylsilane 
• 136366-01-3 (Z)-1-benzoyl-2-phenylethenyltrimethylsilane 
• 100905-28-0 (Z)-1-trimethylsilyl-1-hexenyl phenyl ketone 
• 136366-03-5 (E)-1-benzoyl-1-hexenyltrimethylsilane 

Relevant academic research and scientific papers

STEREOSELECTIVE SYNTHESIS AND CHARACTERIZATION OF 2-ALKYL AND 2-(HETERO)ARYL SUBSTITUTED (Z)- AND (E)-1-TRIMETHYLSILYL-1-TRIMETHYLSTANNYLETHENES

The regio- and stereoselective syntheses of the (Z)- and (E)-stereoisomers of some 1-trimethylsilyl-2-(hetero)arylethenylstannanes and 1-trimethylsilyl-2-alkylethenyltrimethylstannanes of general formula (Z)-2, (E)-2, (Z)-3, and (E)-3, respectively, are reported.The strategy followed to prepare (Z)-2, (E)-2, and (E)-3, involves: a) stereoselective cis- and trans-hydroalumination of the corresponding 1-alkynylsilanes; b) conversion of the stereodefined 1-alkenyl-1-silylalanes so obtained into the corresponding aluminates; and c) the cuprous iodide-triethyl phosphite complex mediated reaction of these aluminates with trimethyltin chloride.Compounds (Z)-3, have been prepared by carbocupration of ethynyltrimethylsilane, 12, followed by treatment with trimethyltin chloride.Compounds (Z)-2, (E)-2, (Z)-3, and (E)-3, have been characterized by MS spectrometry and 1H NMR spectroscopy and their configuration has been unambiguously assigned by 119Sn NMR spectroscopy.The results of an attempt to syntesize a 2-alkyl substituted (E)-1-trimethylsilyl-1-trimethylstannyl-2-arylethene are also discussed.

FORMATION OF α-SILYLVINYLLITHIUM REAGENTS: REACTIONS OF α-SILYL- AND α-STANNYL-VINYLLITHIUMS WITH ALDEHYDES AND KETONES

The formation of α-trimethylsilylvinyllithium compounds from 1-trimethylsilyl-1-trimethylstannyl-1-alkenes have been studied and their stabilities investigated. α-Trimethylsilyl- and α-trimethylstannyl-vinyllithiums undergo 1,2-addition to aldehydes and non-enolisable ketones, to give silyl- or stannyl-substituted allylic alcohols; α,β-unsaturated ketones, however, undergo 1,4-addition to give homoallylic ketones.

α-METALLATED VINYL CARBANIONOIDS. I. FORMATION OF α-STANNYLVINYL ANIONOIDS FROM 1,1-BIS(TRIMETHYLSTANNYL)ALKENES

Hydrostannation of 1-stannyl-1-alkynes leads to the formation of 1,1- and 1,2-distannyl-1-alkenes.The former can undergo lithiation (by alkyllithium in THF) with varying degrees of stereospecificity. 1,1-Dilithio-1-alkenes cannot be prepared by double lit