34881-07-7

Upstream product

• 762-04-9 phosphonic acid diethyl ester 
• 93-55-0 1-phenyl-propan-1-one 
• 762-04-9 Diethyl phosphonate 
• 93-54-9 1-Phenyl-1-propanol 
• 814-49-3 diethyl chlorophosphate 

Downstream Products

• 1530-03-6 1,1-diphenylpropane 
• 152076-78-3 butane-1,1,2-triyltribenzene 
• 80255-45-4 (+/-)-diethyl (1-hydroxy-1-phenylpropyl)phosphonate 

Relevant academic research and scientific papers

Substitution of Secondary Benzylic Phosphates with Diarylmethyl Anions

Substitution of diethyl and diphenyl benzylic phosphates, Alk-CH(Ar1)OP(O)(OR)2 (R = Et, Ph; Alk = Me, Et, i-Pr; Ar1 = aryl), with the anions derived from Ar2CH2 (Ph2CH2,9H-xanthene and fluorene) and n-BuLi at –15 °C was studied. For phosphates with Me as an Alk, diethyl phosphates produced Me-CH(Ar1)CH(Ar2)2 (Ar1 = 4-halo-, 4-CN, 4-Me-, 2-Me, 2-Br-, 3-MeO-phenyl and 2-naphthyl). However, an unwanted substitution at the Et group competed with phosphates of Alk = Et- and i-Pr. Fortunately, the corresponding diphenyl phosphates cleanly underwent the desired substitution. Two enantioenriched phosphates, MeCH(Ph)OP(O)(OEt)2 and EtCH(Ph)OP(O)(OPh)2, proceeded with complete inversion of the stereochemistry.

Deprotonation of secondary benzylic phosphates - configuratiionally stabite benzylic carbanions with a diethoxyphosphoryloxy substituent and their rearrangement to optically active tertiary α-hydroxyphosphonates

Optically active alcohols (ee ≥ 98%) such as 1-phenylpropanol, l-(2-naphthyl)ethanol, 1-tetralol, and 1-indanol were transformed into diethyl phosphates 7a-d. sBuLi/TMEDA -induced phosphate-phosphonate rearrangement in diethyl ether furnished tertiatry α-hydroxyphosphonates 8a-d of high enantiomeric purity (ee 94-98%) in yields of 43-83% with retention of configuration. The enantiomeric excesses were determined by using homochiral (-butyl(phenyl)phosphinothioic acid as chiral solvating agent. VCH Verlaiseesellschaft mbH, 1996.