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2-TRIMETHYLSILYL-1,3-DITHIANE
Boiling Point: 85° / 1
EINECS Number: 236-504-4
Molecular Weight: 192.42
Specific Gravity: 1.014
Flashpoint: 96°C (205°F)
HMIS Key: 2-1-1-X
Hydrolytic Sensitivity: 4: no reaction with water under neutral conditions
Formula: C7H16S2Si
Refractive Index: 1.5330
Application: Review of synthetic utility.1
Employed in synthesis of acylsilanes.2
With BrF3 converts the oxygen of aldehydes and ketones to difluoromethyl groups.3
Used in the preparation of acylsilanes.4
Used in the preparation of unsaturated dithioketene acetals in a Peterson reaction.5
Important reagent for Type I Anion Relay Chemistry (ARC).6
Reference: 1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 604-609.
2. Corey, E. J. et al. J. Am. Chem. Soc. 1967, 89, 434.
3. Cohen, O. et al. Tetrahedron 2009, 65, 1361.
4. Brinkmeyer, R. S. Tetrahedron Lett. 1979, 20, 207.
5. Carey, F. A.; Court, A. S. J. Org. Chem. 1972, 37, 4474.
6. Smith, A. B., III; Wuest, W. M. Chem. Commun. 2008, 5883.
Fieser: F&F: Vol. 4, p 284; Vol. 10, p 380.
Silanes