Peroxyacids epoxidations

Hydroxy-terminated polybutadiene (8) (HTPB) has been treated with dinitrogen pentoxide in methylene chloride. The product (9) is an energetic oligomer but is unlikely to find application because of the inherent instability of /3-nitronitrates." Initial peroxyacid epoxidation of some of the double bonds of HTPB followed by reaction with dinitrogen pentoxide yields a product containing vtc-dinitrate ester groups and this product (NHTPB) is of much more interest as an energetic binder (see Section 3.10)." ... 

A peroxyacid epoxidizes an alkene by a concerted electrophilic reaction where several bonds are broken and several are formed at the same time. Starting with the alkene and the peroxyacid, a one-step reaction gives the epoxide and the acid directly, without any intermediates. 

Peroxyacids epoxidize alkenes in a one-step (concerted) process. 

The peroxyacid epoxidation is quite general, with electron-rich double bonds reacting fastest. The following reactions are difficult transformations made possible by this selective, stereospecific epoxidation procedure. The second example uses magnesium monoper-oxyphthalate (MMPP), a relatively stable water-soluble peroxyacid often used in large-scale epoxidations. These aqueous MMPP epoxidations, carried out at neutral pH to avoid opening the epoxide, avoid the large-scale use of hazardous chlorinated solvents. 

Using the peroxyacid epoxidation of an alkene and the ring opening of an epoxide, devise a two-step synthesis of 1,2-butanediol from 1-butene. 

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