2-Trimethylsilyl-1,3-dithiane

• Catalog No.: L00979
• CAS Number: 13411-42-2
• M. F.: C7H16S2Si
• M. W.: 192.41744
• Purity: 98+%

SYNONYMS

• Title: 2-三甲基硅基-1,3-二噻烷
• IUPAC name: 1,3-dithian-2-yltrimethylsilane
• IUPAC Traditional name: 1,3-dithian-2-yltrimethylsilane

DATABASE IDS

• Beilstein Number: 1616463
• EC Number: 236-504-4
• CAS Number: 13411-42-2
• MDL Number: MFCD00006655

PROPERTIES

• Purity: 98+%
• Boiling Point: 54-55°C/0.17mm
• Density: 1.040
• Flash Point: 96°C(204°F)
• Refractive Index: 1.5330
• TSCA Listed: 否

REFERENCES

• The lithio-derivative undergoes Peterson-type olefination (see Appendix 4) with aldehydes and ketones to give the ketene dithioacetals, useful intermediates in a variety of reactions: J. Org. Chem., 37, 1926 (1972); J. Chem. Soc., Perkin 1, 2272 (1973); Chem. Ber., 106, 2277 (1973). Further reaction with carbonyl compounds provides, after deprotection, a useful -lactone synthesis. An alternative PhSeCl-promoted ring closure, followed by selenoxide elimination gives the butenolide: J. Org. Chem., 45, 2236 (1980):
  
• For a review of the chemistry of ketene dithioacetals, see: Synthesis, 171 (1990).
• Tandem bis-alkylation with epoxides provides a route to enantiopure 1,5-diols and related compounds; the key step is a [1,4] Brook rearrangement of the initially-formed alkoxide: Synlett, 511 (1994):
  
• Review of the chemistry of mixed organosulfur/organosilicon compounds: Tetrahedron, 44, 281 (1988).