Alkoxyphosphonium salts synthesis

Miscellaneous. The reaction of the aminophosphonium salt (156) with thiols and alkoxides affords a convenient, high-yield, single-step synthesis of unsymmetrical thioethers.141 The key intermediate is the alkoxyphosphonium salt (157), which undergoes nucleophilic attack by RS- at the alkoxy carbon. 

In view of the usefulness of alkoxyphosphonium salts in synthesis it is of interest to note that, depending on the mode of addition of the... 

Rajendran KV, Kudavalli JS, Dunne KS, Gilheany DG (2012) A U-tum in the asymmetric Appel reaction stereospecific reduction of diastereomerically cairiched alkoxyphosphonium salts allows the asymmetric synthesis of P-stereogenic phosphanes and phosphane boranes. Eur J Org Chem 2720-2723... 

Synthesis.—Alcohols can be induced to act as electrophiles in a modified Gabriel amine synthesis alkoxyphosphonium salts efficiently alkylate phthalimide and other imides (Scheme 119) with almost complete inversion... 

OL-Alkoxyphosphonium bromides enol ethers. These salts (2) are prepared by reaction of an enol ether (1) with triphenylphosphine hydrobromide at 0 —> 20° in CH2CI2 in 85-90% yield. The ylides formed on deprotonation undergo Wittig reactions to give enol ethers (3), which are suitable for further transformations. An example is the synthesis of a C-glycoside (4). 

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