71421-27-7

Basic information

• Product Name: 4-Cyclohexyl-4-methoxy-1-H-1-methyl-1-silacyclohexa-2,5-dien
• CAS NO: 71421-27-7
• Molecular Weight: 222.403
• Mol File: 71421-27-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-Cyclohexyl-4-methoxy-1-H-1-methyl-1-silacyclohexa-2,5-dien(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Cyclohexyl-4-methoxy-1-H-1-methyl-1-silacyclohexa-2,5-dien(71421-27-7)
• EPA Substance Registry System: 4-Cyclohexyl-4-methoxy-1-H-1-methyl-1-silacyclohexa-2,5-dien(71421-27-7)

Safety Data

• Hazardous Substances Data: 71421-27-7(Hazardous Substances Data)

Upstream product

• 75-54-7 Dichloromethylsilane 
• 51470-93-0 1,1-di-n-butyl-4-cyclohexyl-4-methoxy-1,4-dihydrostannane 

Downstream Products

• 343596-96-3 1-Chlor-4-cyclohexyl-1-methyl-6-trimethylsilyl-1-silacyclohexa-2,4-dien 
• 71421-60-8 1H-1-methyl-4-cyclohexyl-1-silacyclohexa-2,4-dien 

Relevant articles and documents

SILACYCLOHEXADIENYLANIONEN BIS- UND TRIS-(TRIMETHYLSILYL)-SILACYCLOHEXADIENE

1,1-Dialkyl(1,1-diaryl)-4-R-1-silacyclohexadienyl anions (1) are available by ether cleavage of the corresponding 1,1-dialkyl(1,1-diaryl)-4-methoxy-4-R-1-silacyclohexa-2,5-dienes (4), or by deprotonation of the 1,1-dialkyl(1,1-diaryl)-4-R-1-silacyclohexa-2,4-dienes (3) - which are available from 4 - with n-BuLi or LDA resp.The anions 1 are regioselectively silylated by trimethylchlorosilane to give the 6-trimethylsilyl-1-silacyclohexa-2,4-dienes (7,8), their alkylation or acylation occurs exclusively in 4-position to 16 or 17 resp.Deprotonation of 7, 8 with n-BuLi gives the 2-trimethylsilyl-1-silacyclohexadienyl anions (9), with trimethylchlorosilane they react regioselectively to give the 2,6-bis(trimethylsilyl)-1-silacyclohexa-2,4-dienes (10, 11), with alkyl halides and ketones the anion 9 reacts only in the 4-position.The 1-silacyclohexa-2,5-dienes 22, 25, 28 substituted at the silicon atom by functional groups (O-i-Prop) or by hydrogen can be transformed into 2,6-bis(trimethylsilyl)-1-silacyclohexa-2,4-dienes 24, 27, 33 resp., if LDA is used as base.The easily formed 4-R-2,6-bis(trimethylsilyl)-1-silacyclohexa-2,4-dienyl anions (by deprotonation of 10, 11, 24, 27, 33 with LDA) react with trimethylchlorosilane regioselectively to give 4-R-2,4,6-tris(trimethylsilyl)-1-silacyclohexa-2,5-dienes 37.Accessing 37 succeeds very simply by manifold-silylation of the 1-sila-2,4-cyclohexadienes 38 with excess trimethylchlorosilane in the presence of 3 mol LDA.Owing to trimethylsilyl substitution in the 2,6-position of the 1-silacyclohexa-2,4-dienes, the ring-silicon atom is strongly sterically shielded, therefore reactions of functional groups at the silicon atom are restricted.