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Mercuration of some styrenes and phenylcyclopropanes. The effect of the aromatic nitro group on reductive demercuration with sodium borohydride by Yu.S. Shabarov; S.S. Mochalov; T.S. Oretskaya; V.V. Karpova is a Chemistry article available to read on EtoBox.

What is Mercuration of some styrenes and phenylcyclopropanes. The effect of the aromatic nitro group on reductive demercuration with sodium borohydride about?

Mercuric acetate reacts with o-and p-nitrostyrenes and with nitrophenylcyclopropaues in methanol or glacial acetic acid to give /3-and T-mercurated nitroderivatives, respectively. In contrast to the nitrostyrenes, mercuration of the corresponding nitrophenylcyclopropanes only occurs in the presence of perchloric acid as catalyst. 2,4-Dinitrophenylcyclopropane does not reac-.; with mercuric acetate even under the catalysis conditions. Aromatic nitro groups decelerate reductive demercnration of y-mercurated alcohols and their derivatives with sodium borohydride to the extent that other fragments of the molecule may undergo reduction while the HgX function remains intact. This result may be explained by intermolecular coordination of the nitro group to the mercury atom, which reduces effective positive charge on the metal and hinders the attack by the reducing reagent. . . ## pan& ring bp&ing under the &ion of strong klectrophiles such as concentrated sulphuric acid [S-IO]. It is thereftire reasonable to expect that increase in-electrophilic power of the mercurating reagent \* would favour mercuration of phenylcyclopropanes containing electron withdrawing substituents ix-the benzene n

Who reads Mercuration of some styrenes and phenylcyclopropanes. The effect of the aromatic nitro group on reductive demercuration with sodium borohydride?

Author

Yu.S. Shabarov; S.S. Mochalov; T.S. Oretskaya; V.V. Karpova

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0022-328X)

Published

1978

Language

EN

Field

Chemistry (Physical Sciences)