90270-49-8

Basic information

• Product Name: 4,4-dimethyl-3-trimethylsilyloxy-1-pentene
• Synonyms: 4,4-dimethyl-3-trimethylsilyloxy-1-pentene
• CAS NO: 90270-49-8
• Molecular Weight: 186.37
• Mol File: 90270-49-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4,4-dimethyl-3-trimethylsilyloxy-1-pentene(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-dimethyl-3-trimethylsilyloxy-1-pentene(90270-49-8)
• EPA Substance Registry System: 4,4-dimethyl-3-trimethylsilyloxy-1-pentene(90270-49-8)

Safety Data

• Hazardous Substances Data: 90270-49-8(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 1471-04-1 allyl tert-butyl ether 

Downstream Products

• 90270-83-0 erythro-3-(p-nitrophenyl)-5-<(1S)-1-(trimethylsilyloxy)-2-methylpropyl>-2-isoxazoline 

Relevant articles and documents

THE WITTIG REARRANGEMENT AS A PRACTICAL METHOD FOR ALDEHYDE SYNTHESIS

If the rearrangement of metalated allyl ethers 2 (or 4) is accomplished in the presence of potassium tert-butoxide, primary alkyl groups preferentially migrate to the unsubstituted allylic terminus (γ-position).Enolates 7 and 1-vinylalcoholates 6 (by alkyl migration to the α-position, adjacent to the oxygen atom) are produced in an approximate ratio of 9 : 1.Because of the endo-configuration of their organometallic precursors, the enolates exclusively emerge in the (Z)-configuration as shown by trapping with chlorotrimethylsilane and isolation of the resulting O-silyl (Z)-enethers.Hydrolysis of the latter affords the corresponding aldehydes with good yields. -The rearrangement is mechanistically still obscure.A concerted process as the main reaction mode is unlikely.The intermediacy of zwitterionic metallomers 18 and solvent caged radical pairs 17 is tentatively suggested.