93085-47-3

Upstream product

• 100-52-7 benzaldehyde 
• 89996-01-0 (3-aminopropyl)(triphenyl)phosphonium bromide 
• 143741-67-7 N-(4-phenyl-3-butenyl)phthalimide 

Downstream Products

• 126376-92-9 N-(4-phenyl-3-cis-butenyl)-1H-imidazole-4-ethanamine 
• 1229026-39-4 (Z)-2-(4-phenyl-3-butenyl)-2H-indazole-3-carbonitrile N-oxide 
• 428453-34-3 (Z)-4-methyl-N-(4-phenylbut-3-en-1-yl)benzenesulfonamide 
• 428453-46-7 N-(4-nitrophenylsulfonyl)-(Z)-4-phenyl-but-3-enylamine 

Relevant academic research and scientific papers

Convenient route to primary (Z)-allyl amines and homologs

A convenient two-step procedure for the synthesis of primary (Z)-allyl amines, (Z)-homoallyl amines [(Z)-but-3-enylamines], and (Z)-pent-4-enylamines using the Wittig reaction was achieved. The use of nonstabilized ylides from triphenylphosphonium salt, potassium salt, and apolar solvent produced (Z/E)-geometric isomer ratios generally greater than 1.6. The amine moiety was masked using a phtalimide group that was removed successfully in the last step of the process in two different conditions, NH2NH2/EtOH/rt or CH3NH2/EtOH/rt. However, in some cases, reduction of the C = C double bond in the deprotection with hydrazine was concomitantly observed. Copyright Taylor & Francis Group, LLC.

ANOMALOUS STEREOCHEMISTRY IN THE WITTIG REACTION INDUCED BY NUCLEOPHILIC GROUPS IN THE PHOSPHONIUM YLIDE

Reaction of ylides from 3-9 with benzaldehyde show that carboxylate and oxido functionalities proximate to the ylide center promote anomalously high E stereoselectivity in alkene formation.Through the use of α-deuterated ylides 12-14, an internal "trans-selective Wittig" mechanism was ruled out as a principal source of exaggerated E alkene production.