Silane, trimethyl(2-methylene-3-buten-1-yl)-
- CAS No.
- 70901-64-3
- Chemical Name:
- Silane, trimethyl(2-methylene-3-buten-1-yl)-
- Synonyms
- Silane, trimethyl(2-methylene-3-buten-1-yl)-
- CBNumber:
- CB36167698
- Molecular Formula:
- C8H16Si
- Molecular Weight:
- 140.3
- MDL Number:
- MOL File:
- 70901-64-3.mol
Silane, trimethyl(2-methylene-3-buten-1-yl)- Chemical Properties,Uses,Production
Physical properties
bp 69–70 °C/80 mmHg.
Uses
2-Trimethylsilylmethyl-1,3-butadiene is an isoprenylation reagent; Diels–Alder diene; reactant in Formation of π-Allylic Complex Followed by Acyldemetalation.
Preparation
2-Trimethylsilylmethyl-1,3-butadiene is prepared most conveniently by the coupling reaction of the Grignard reagent prepared from (chloromethyl)trimethylsilane with 2-chloro-1,3-butadiene (chloroprene) in the presence of a catalytic amount of Ni[Ph2P- (CH2)3PPh2]Cl2 (91% yield) (eq 1). Alternatively, it can be prepared by the reaction of the same Grignard reagent with allenylmethyl phosphate in 57¨C73% yield (eq 2). Direct metalation of isoprene followed by the reaction with chlorotrimethylsilane gives 2-trimethylsilylmethyl-1,3-butadiene in low yield. Thermal isomerization of 1-trimethylsilylmethylcyclobutene to 2-trimethylsilylmethyl-1,3-butadiene has also been reported.
