Phenyl vinyl sulfone, 99+%
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Reactive dienophile. Can function as an acetylene equivalent if benzenesulfinic acid is eliminated thermally from the Diels-Alder adduct to form an olefinic double bond: J. Am. Chem. Soc., 100, 1597 (1978).
Can also behave as an activated form of ethylene if the sulfone group is cleaved from the adduct, e.g. with Na amalgam, with the possibility of prior alkylation of the adduct: J. Org. Chem., 48, 4976 (1983):
For addition to 1-Methoxy-3-trimethylsiloxy-1,3-butadiene, L06100, see: J. Org. Chem., 48, 4986 (1983). Addition to steroids with a cyclopentadienoid D-ring, followed by cleavage of the resulting alkene, gives the diformyl derivatives, useful for further functionalization: J. Chem. Soc., Perkin 1, 241 (1990).
For use in a 1,3-dipolar cycloaddition reaction, see 3-Hydroxypyridine, A13910.
Undergoes the Baylis-Hillman reaction (addition to aldehydes in the presence of 1,4-Diazabicyclo[2.2.2]octane, A14003): Tetrahedron, 44, 6095 (1988).
See also Divinyl sulfone, L12827.
|Harmonized Tariff Code:||2930.90|
GHS Hazard and Precautionary Statements
Causes skin irritation. Causes serious eye irritation. May cause an allergic skin reaction. May cause respiratory irritation.
Wear protective gloves. Do not get in eyes, on skin, or on clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
Risk & Safety
|Irritating to eyes, respiratory system and skin. May cause sensitisation by skin contact.|
|Avoid contact with skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Wear suitable gloves.|