Influence of Nucleophilic Reagents on the Reactions of Phosphorus Sulfides and Alkyl Homologues of Davy's Reagent With Alkyl Halides and Dialkyl Disulfides

Abstract

Use of potassium carbonate, sodium sulfide and sodium alkylthiolates results in the reactivity enhancement of phosphorus sulfides (P4Sl0, P4S, and P4S5) and alkyl homologues of Davy's reagent in their reactions with alkyl halides and dialkyl di sulfides.

A Berzelius Reagent, Phosphorus Decasulfide (P4S10), in Organic Syntheses

“…Reaction of benzyl chloride with P 4 S 10 in the presence of K 2 CO 3 in acetonitrile (dry) at 60−70 °C for 2 h gave tribenzyltetrathiophosphate (PhCH 2 S) 3 PS. , …”

“…Reaction of benzyl chloride with P 4 S 10 in the presence of K 2 CO 3 in acetonitrile (dry) at 60-70 °C for 2 h gave tribenzyltetrathiophosphate (PhCH 2 S) 3 PdS. 446,447 Treatment of coumarine 597, having an azido and a carboxaldehyde at 4-and 3-carbons, respectively, with P 4 S 10 in refluxing toluene resulted in the formation of two unusual products, 598 and 599 (Scheme 150). 448…”

Synthesis of Tetrathiophosphates from White Phosphorus

“…[ 18 ] In 1997, the cheap sodium sulfide was chosen to enhance the reactivity of these reactions (Scheme 1D‐c). [ 19 ]…”

Synthesis of Tetrathiophosphates from White Phosphorus

“…18 In 1997, the cheap sodium sulfide was chosen to enhance the reactivity of these reactions (Scheme 1D-c). 19 To circumvent the use of PCl 3 and complicated organophos-phorus transfer reagents, much effort has been invested over several decades into the development of alternative, direct transformations of P 4 into useful OPCs. However, while the past few years have begun to see some progress in this area, [8][9][10]20 direct organofunctionalisation of P 4 remains in its infancy.…”