100281-23-0

Upstream product

• 558-13-4 carbon tetrabromide 
• 79074-00-3 2,4,6-tri-t-butylphenylphosphonous dichloride 
• 84751-28-0 2-(2,4,6-tri-tert-butylphenyl)-1,1-bis(trimethylsilyl)phosphaethene 
• 111888-02-9 (1R,2R)-3,3-Dibromo-1,2-bis-(2,4,6-tri-tert-butyl-phenyl)-diphosphirane 
• 118281-77-9 (Diiodomethylene)(2,4,6-tri-tert-butylphenyl)phosphine 

Downstream Products

• 100938-86-1 2-(2,4,6-tri-tert-butylphenyl)phosphaacetylene 
• 100281-28-5 [1-Bromo-eth-(Z)-ylidene]-(2,4,6-tri-tert-butyl-phenyl)-phosphane 
• 195618-90-7 6,8-Di-tert-butyl-4,4-dimethyl-1-phospha-3,4-dihydronaphthalene 
• 301336-03-8 2,4,6-Tris(2,4,6-tri-tert-butylphenyl)-1,3,6-triphosphafulvene 
• 517877-22-4 (1,5-dibromo-pentylidene)-(2,4,6-tri-tert-butyl-phenyl)-phosphane 
• 662112-27-8 2-bromo-3-methoxy-1-phosphapropene 
• 716379-89-4 (1-bromo-2-methoxy-2-phenyl-ethylidene)-(2,4,6-tri-tert-butyl-phenyl)-phosphane 
• 879981-64-3 (1-bromo-2-cyclopropyl-2-methoxy-ethylidene)-(2,4,6-tri-tert-butyl-phenyl)-phosphane 
• 862852-62-8 2-bromo-3-phenyl-1-(2,4,6-tri-tert-butylphenyl)-3-trimethylsiloxy-1-phospha-1-propene 
• 954415-81-7 2-bromo-3-(4-cyanophenyl)-1-(2,4,6-tri-tert-butylphenyl)-1-phosphaprop-1-ene 
• 26026-46-0 cis-[PtBr₂(PPh₃)2] 
• 156429-51-5 Pt(Br)(P(C₂H₅)3)2(C(Br)PC₆H₂(C(CH₃)3)3) 
• 177902-38-4 ((CH₃)3C₆H₂)2Ge(F)(C(Br)PC₆H₂(C(CH₃)3)3) 
• 952650-64-5 2-bromo-3-(2-thienyl)-1-(2,4,6-tri-t-butylphenyl)-3-(trimethylsiloxy)-1-phosphapropene 

Relevant academic research and scientific papers

C-Halophosphaalkenes: probing the range of stability and reactivity towards bromine

The importance of steric protection for the stability of phosphaalkenes RP=CI2 (6) was investigated by varying the size of group R.The phosphaalkene IsP=CI2 (6b) (Is = 2,4,6-triisopropylphenyl) could be prepared in 15percent isolated yield by reaction of IsPCl2 and HCI3 with two equivalents of lithium diisopropylamide, in analogy to the synthesis of the stable, sterically more protected, Mes*P=CI2 (6a) (Mes* = 2,4,6-tri-tert-butylphenyl).If the steric protection on the phosphorus eas decreased further (R = Es = 2,4,6-triethylphenyl, R = Mes = 2,4,6-trimethylphenyl), the substitution products RP(Cl)N(i-Pr)2 (R = Es (9c) or Mes (9d)) were formed as main products, in addition to thermally unstable phosphaalkenes EsP=CI2 (6c) and MesP=CI2 (6d).The structures of 9c-d were corroborated by independent synthesis from RPCl2 and two equivalents of diisopropylamine.The reaction of 6a with bromine gave an E/Z mixture of the C-bromo-C-iodophoaphaalkene (EZ)-Mes*P=CBrI (E/Z-10).Further reaction with bromine proceeded via Mes*P=CBr2 (5a) and finally led to Mes*P(Br)(CHBr2) (12).

Photochemistry of Functionalized Diphosphiranes

The structure of the functionalized trans-diphosphiranes 1a-e, obtained by reaction of halogenocarbenes with the trans-diphosphene is confirmed by X-ray diffraction.The photolysis of 1a-e lead to the functionalized cis- and trans-1,3-diphosphapropenes 2a-e as major products, via the diphosphiranyl 7 and the diphosphapropenyl 8 radical intermediates.The latter are characterized by ESR spectroscopy using the spin-trap method.The trans configuration of 2a is also confirmed by X-ray diffraction.The mechanism of the ring-opening, involving P-P bond rupture, is discussed.

SYNTHESE UND REAKTIONEN DER 2,4,6-TRI-TERT-BUTYLPHENYLDIHALOGENMETHYLENPHOSPHANE1

The synthesis of dihalogenated phosphaalkanes 2a,b is reported.After metallation with n-BuLi they could be substituted by halogenated compounds.