The modern interpretation of the Wittig reaction mechanism

Abstract

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Synthesis of olefins via a Wittig reaction mediated by triphenylarsine

“…We reasoned that acetonitrile was a better solvent than THF or toluene due to the reduced nucleophilicity of arsine versus phosphine, 28–30 as polar solvents accelerate the rate of binuclear substitutions. We therefore next investigated a pseudo-one-pot reaction 31 to both support our hypothesis and improve isolated yields of the olefin (Table 1). …”

Third-Liquid Phase Transfer Catalysis for Horner–Wadsworth–Emmons Reactions of “Moderately Acidic” and “Weakly Acidic” Phosphonates

“…Cycloaddition transition states (TS) for OPA formation have two conformation -cis TS (puchered) and trans TS (planar), thereby generating corresponding Z-product and E-product. 48 Generally, for HWE reaction, geometric selectivity is governed by 1,2 interaction. P-Cl bond and QA interaction in TS are generated and can influence geometric selectivity (Fig.…”

Catalytic Wittig and aza-Wittig reactions

“…Since its introduction over half a century ago [1–2], it has been widely employed in organic synthesis due to its versatility and reliability. The requirement of simple and inexpensive reagents to generate the necessary phosphonium ylide (phosphorane) reactant (a phosphine, typically Ph 3 P ( 1 ), an alkyl halide and a base), also adds to its appeal [3–4].…”