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13411-42-2 - 2-Trimethylsilyl-1,3-dithiane, 98+% - L00979 - Alfa Aesar

L00979 2-Trimethylsilyl-1,3-dithiane, 98+%

CAS Number
13411-42-2
Synonyms

Size Price ($) Quantity Availability
5g 70.20
25g 280.00
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2-Trimethylsilyl-1,3-dithiane, 98+%

MDL
MFCD00006655
EINECS
236-504-4

Chemical Properties

Formula
C7H16S2Si
Formula Weight
192.42
Boiling Point
54-55°/0.17mm
Flash Point
96°(204°F)
Density
1.040
Refractive Index
1.5330

Literature 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):

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For a review of the chemistry of ketene dithioacetals, see: Synthesis, 171 (1990).

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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):

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Review of the chemistry of mixed organosulfur/organosilicon compounds: Tetrahedron, 44, 281 (1988).

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Other References

Beilstein
1616463
Harmonized Tariff Code
2934.99
TSCA
No

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