179989-93-6

Upstream product

• 13292-87-0 dimethylsulfide borane complex 
• 707-61-9 3-Methyl-1-phenyl-2-phospholene 1-oxide 
• 1416656-01-3 (S)-methyl(3-methylbut-3-en-1-yl)phenylphosphine borane 
• 35512-87-9 dimethylphenylphosphine borane 
• 1416656-14-8 (S)-methyl(3-methylbut-3-en-1-yl)phenylphosphine borane 
• 1416656-12-6 C₁₃H₂₂BOP 
• 644-97-3 Dichlorophenylphosphine 
• 1416656-03-5 (R)-ethenyl(3-methylbut-3-en-1-yl)phenylphosphine borane 
• 17154-12-0 1-chloro-3-methyl-1-phenyl-2-phospholenium salt 
• 7564-51-4 2,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide 
• 1416656-01-3 methyl(3-methylbut-3-en-1-yl)phenylphosphine borane 
• 1416656-03-5 ethenyl(3-methylbut-3-en-1-yl)phenylphosphine borane 
• 1416656-12-6 2-boranyl(3-methylbut-3-en-1-yl)(phenylphosphaniumyl)ethan-1-ol 

Downstream Products

• 179989-94-7 4-methyl-1-phenyl-2,3-dihydro-1H-phosphole-dichloromethylborane 
• 179989-96-9 6,6-dichloro-1-methyl-4-phenyl-4-phosphabicyclo[3.1.0]hexane-dichloromethylborane 
• 200512-77-2 3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-phosphole-dichloromethylborane 

Relevant academic research and scientific papers

A novel preparation of chlorophospholenium chlorides and their application in the synthesis of phospholene boranes

A novel preparation of 1-chloro-3-methyl-3-phospholenium chlorides was developed by reacting 1-substituted-3-methyl-3-phospholene 1-oxides with oxalyl chloride. The obtained cyclic chlorophosphonium salts were reacted with LiBH4to afford the corresponding 1-substituted-3-methyl-3-phospholene boranes. The latter protocol involves a silane-free deoxygenation, and borane complex formation. In one instance, a 2-phospholene borane and the corresponding P-oxide were synthesized via rearrangement of the double bond in the cyclic chlorophosphonium salt. This double bond migration was investigated by quantum chemical calculations.

Synthesis of P-stereogenic phospholene boranes via asymmetric deprotonation and ring-closing metathesis

The first examples of the asymmetric synthesis of P-stereogenic vinylic phospholene boranes are described. The synthetic approach is concise and flexible. The route involves (i) asymmetric deprotonation-allylation of a dimethyl phosphine borane; (ii) telescoped regioselective deprotonation, paraformaldehyde trapping, and hydroxyl group elimination to give a diene; and (iii) ring-closing metathesis.

Synthesis of phosphine-borane complexes of P-heterocycles

Dihydro-1H-phosphole-boranes 5 and 10 were prepared from phosphine oxides 1 and 9 respectively. Reaction of borane 5 with dichlorocarbene gave dihydrophosphole-dichloromethylborane 6 and tetrahydro derivative 7a as the main products, and dichlorocycloprop