By Sosman R.B.
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Extra resources for An Outline of Geophysical-Chemical Problems (1920)(en)(10s)
Are very effective catalysts in the epoxidation of electron-poor olefins with hydrogen p e r o ~ i d e . ’ ~ ’ Oxides , ~ ~ ~ -of~ ~ ~ tungsten and molybdenum are most frequently employed; in the presence of hydrogen peroxide these are oxidized to peracids and as a consequence of the catalytic activity of the peroxyanions (HWO;, HMoO;), the rate of the epoxidation is enhanced considerably. Pertungstic acid is formed rapidly: H2W04 + H202+ H2WOs + H 2 0 . Its anion exists in a cyclic form involving an intramolecular hydrogen bond (Eq.
670,671 The mechanism of a-halooxirane formation is illustrated in Eq. 98. Reactions of Oxiranes (Me,N),P R' + R'CCl, - 0 (Me,NI3P I 0 C-R I c1 c1, - 57 R21C,0 H' (98) = C 0 2 R , CONHz It has been established that the alcoholates formed are very reactive. The aldolization is always reversible and, regardless of whether direct or secondary cyclization occurs, only the trans product is obtained. 672 X = C1, Br, C1O4 L = pyridine, etc. , Cu(OCH3)Clpyridine) (Eq. 673 IV. REACTIONS OF OXIRANES The chemical behavior of oxiranes is governed by two factors: the strain in the ring and the basicity of the ring.
R O A ; 0.. Lf Li 90 Oxiranes may also be prepared from the reaction of aldehydes with trivalent phosphorus derivatives, as in Eq. 97. 2 ArCHO + (R2N)3P - A r T Ar + (R2N)3P=0 (97) 0 The interpretation of the mechanism of the reaction is that the trivalent phosphorus attacks the oxygen of the aldehyde, after which diastereomeric dioxaalkane intermediates 91,92 are obtained with another molecule of aldehyde. 670,671 The mechanism of a-halooxirane formation is illustrated in Eq. 98. Reactions of Oxiranes (Me,N),P R' + R'CCl, - 0 (Me,NI3P I 0 C-R I c1 c1, - 57 R21C,0 H' (98) = C 0 2 R , CONHz It has been established that the alcoholates formed are very reactive.