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Bridging Silicon-Based Blocking Agent
Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.
1,2-Bis(dimethylsilyl)benzene; Dimethylsilphenylene; BSB
Boiling Point: 129° / 50
Molecular Weight: 194.42
Specific Gravity: 0.893
Flashpoint: 71°C (160°F)
HMIS Key: 2-2-1-X
Hydrolytic Sensitivity: 3: reacts with aqueous base
Refractive Index: 1.511
Application: Acetylenes undergo dehydrogenative double silylation to yield cyclics.1
Aldehydes undergo dehydrogenative double silylation to yield disila-2-oxacyclohexanes.2
Reacts with ?-hydroxycarboxylates with Rh to form lactones.3
Employed in the high-yield reduction of amides to amines in the presence of other reducible groups.4
Reference: 1. Tanaka, M. et al. Bull. Soc. Chim. Fr. 1993, 129, 667.
2. Uchimaru, Y. et al. Organometallics 1992, 11, 2639.
3. Mukaiyama, T. et al. Chem. Lett. 1997, 2, 18.
4. Hanada, S. et al. J. Am. Chem. Soc. 2009, 131, 15032.
Fieser: F&F: Vol. 20, p 40.