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Sulfonium fluoroborate, dimethyl catalyst allylstannane reaction with thioacetals

Allylstannanes are much better nucleophiles for dithioacetals than allylsilanes, and dimethyl(methyl-thio)sulfonium fluoroborate is a particularly good catalyst in this reaction. The reaction has been used tellingly in a macrocyclization (Scheme 56). ° Monothioacetals also react with allylstannanes, with cleavage of either the carbon-oxygen or the carbon-sulfur bond, depending upon the choice of Lewis acid (Scheme 57).Sugar thioacetals react in the same way (Scheme 58), but with the opposite anomeric stereoselectivity from that of the corresponding radical chain substitution. ... [Pg.581]


See also in sourсe #XX -- [ Pg.2 , Pg.581 ]

See also in sourсe #XX -- [ Pg.581 ]

See also in sourсe #XX -- [ Pg.581 ]

See also in sourсe #XX -- [ Pg.2 , Pg.581 ]

See also in sourсe #XX -- [ Pg.581 ]




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Allylstannane

Allylstannanes

Dimethyl reactions

Dimethyl sulfonium

Dimethyl sulfonium fluoroborate

Fluoroborates

Reaction with Catalyst

Reactions thioacetalization

Sulfonium

Thioacetal

Thioacetalization

Thioacetate

Thioacetates

With Allylstannane

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