53722-76-2

Upstream product

• 603-32-7 triphenyl-arsane 

Downstream Products

• 5066-67-1 2-Hydroxypropyl-diphenylarsin 
• 53722-81-9 2r,6c-dimethyl-4,4-diphenyl-[1,4]oxarsinanium; bromide 
• 39669-95-9 (E)-hexa-3,5-dien-1-ylbenzene 
• 77605-17-5 (E/Z)-6-phenyl-1,3-hexadiene 
• 25203-83-2 (E)/(Z)-buta-1,3-dien-1-ylcyclohexane 

Relevant academic research and scientific papers

Reactivity of aldehydes with semi-stabilised arsonium ylide anions: Synthesis of terminal (E)-l,3-dienes

A study of the reactivity of semi-stabilised arsonium ylide anions in olefinalion reactions is presented. The different ylide anions were generated by the addition of nBuLi to various arsonium halide derivatives: [Ph 2As(R)R']+X , where R and R′ are methyl, allyl, prenyl or benzyl groups. By using diallyldiphenylarsonium bromide (R = R′ = allyl) an olefinationprotocol was optimised allowing the efficient transformation of aliphatic aldehydes into terminal 1,3-dienes with a high selectivity for the E isomer (E/Z ratios ranging from 90:10 to 97:3). The olefination reactions of aldehydes with dissymmetric arsonium halides (R≠R′) are very chemoselective; with arsonium ylide anions the benzyl moiety is more reactive than the allyl moiety which is much more reactive than prenyl and methyl groups. Based on the experimental results, a mechanism is proposed for the reaction.