86314-34-3

Upstream product

• 86280-12-8 methylenebis(methyldimesitylphosphonium iodide) 
• 86280-11-7 Lithium-bis(2,4,6-trimethylphenyl)phosphid 
• 86280-10-6 Methylenbis 
• 86314-32-1 1,1,3,3,3,4-Hexahydro-2,3-didehydro-1,3,6,8-tetramethyl-1,3-bis(2,4,6-trimethylphenyl)-1,3-benzodiphosphorin 

Relevant academic research and scientific papers

Rearrangements of the Methyltrimesitylphosphonium and Methylenebis(methyldimesitylphosphonium) Cation Skeletons on Treatment with Base

The treatment of methyltrimesitylphosphonium iodide (1) with sodium amide or butyllithium leads neither to the corresponding phosphorus ylide nor to the product of a Stevens rearrangement, but affords instead methylmesitylphosphane (4).The product, which is probably formed via a mesityl migration in an 2-methylenecyclohexadienylidenephosphorane intermediate (2b), is structurally characterized by detailed NMR analysis and through hydrochloride and methoiodide derivatives. - Analogous treatment of methylenebis(methyldimesitylphosphonium iodide) (10) with base leads to a pair of diastereomeric cyclic carbodiphosphoranes (12a, b), with elimination of mesitylene.The two carbodiphosphoranes are converted into the diastereomeric diphosphonium salts 13a, b with HCl.The ring closure leading to carbodiphosphorane formation is again interpreted in terms of an intramolecular process involving an 2-methylenecyclohexadienylidene intermediate.Deprotonation of the methylenebis(methyldi-o-tolylphosphonium) cation yields the corresponding carbodiphosphorane 18 without changes in the skeleton.