(g) Janjic, J. M.; Mu, Y.; Kendall, C.; Stephenson, C. R. J.; Balachandran, R.; Raccor, B. S.; Lu, Y.; Zhu, G.; Xie, W.; Wipf, P.; Day, B. W. Bioorg. Med. Chem. 2005, 13, 157.
We have utilized the reaction of inexpensive PBr3 with α-hydroxyphosphonates also to prepare a series of 2-[aryl(bromo)methyl]-5, 5-dimethyl-1,3,2-dioxaphosphinane 1-oxides (aryl, phenyl, 4-methylphenyl, 4-chlorophenyl, 4-bromophenyl, some of these compound have been previously reported.2a Note that 2-(1-hydroxy-3-phenyl-prop-2-enyl)-5,5- dimethyl-1,3,2-dioxaphosphinane 1-oxide affords two types of cinnamyl-substituted bromophosphonates 2-(1-bromo-3-phenylprop-2-enyl)-5,5- dimethyl-1,3,2-dioxaphosphinane 1-oxide and 2-(3-bromo-3-phenyl-prop-1-enyl)-5, 5-dimethyl-1,3,2-dioxaphosphinane 1-oxide, while the using 2-[hydroxy(2-furyl) methyl]-5,5-dimethyl-1,3,2-dioxaphosphinane 1-oxide affords 2-5-bromo-2-furyl, 5,5-dimethyl-1,3,2-dioxaphosphinane 1-oxide. More details are available from the authors or in ref. 9
2a Note that 2-(1-hydroxy-3-phenyl-prop-2-enyl)-5,5- dimethyl-1,3,2-dioxaphosphinane 1-oxide affords two types of cinnamyl-substituted bromophosphonates 2-(1-bromo-3-phenylprop-2-enyl)-5,5- dimethyl-1,3,2-dioxaphosphinane 1-oxide and 2-(3-bromo-3-phenyl-prop-1-enyl)-5, 5-dimethyl-1,3,2-dioxaphosphinane 1-oxide, while the using 2-[hydroxy(2-furyl) methyl]-5,5-dimethyl-1,3,2-dioxaphosphinane 1-oxide affords 2-(5-bromo-2-furyl)- 5,5-dimethyl-1,3,2-dioxaphosphinane 1-oxide. More details are available from the authors or in ref. 9.
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34249787681
PhD Thesis; University of Hyderabad: India
Pavan Kumar, K. V. P. PhD Thesis; University of Hyderabad: India, 2006.
All data has been deposited at the Cambridge database. We believe that such information will be useful, in case these compounds are pharmacologically active
All data has been deposited at the Cambridge database. We believe that such information will be useful, in case these compounds are pharmacologically active.
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0004055425
Pergamon: Oxford
Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals; Pergamon: Oxford, 1986.