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Encyclopedia of Reagents for Organic Synthesis - Wikipedia
T1 - New silicon-phosphorus reagents in organic synthesis. Carbonyl and conjugate addition reactions of silicon phosphite esters and related systems
Hexamethylenetetramine is a versatile reagent in organic synthesis
The reagent for organic synthesis reversibly changes from a liquid-phase state to a solid-phase state with changes in solution composition and/or solution temperature, and is for use in organic synthesis reactions.
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AB - The 1,2- and 1,4-addition reactions of organosilicon tervalent phosphorus esters, X2POSiR3(X = OMe, NMe2, Ph), with saturated and α,β-unsaturated aldehydes and ketones have been studied. These addition reactions have been compared with the complementary reactions of alkyl phosphorus esters, X2POCH3, and R3SiCl with carbonyl substrates. With α,β-unsaturated aldehydes, a judicious choice of reagent and conditions leads to the regioselective 1,2- or 1,4-addition mode. Some of the mechanistic details of these addition reactions have been elucidated.