By Professor Richard C. Larock (auth.)
The box of organometallic chemistry has loved explosive progress lately. in this time a speedily expanding variety of metals have discovered application in natural synthesis because the corresponding organometallic compounds. The sub ject of "Organic Synthesis by way of Transition steel Complexes" used to be reviewed within the first quantity of this sequence of monographs. This quantity offers essentially with the appli cation of organomercury compounds in natural synthesis (exclusive of solvomercuration-demercuration reactions), yet will of necessity contain a few reactions of different organometallics besides. Organomercurials are one of the oldest identified organo metallics and have been maybe the 1st to have a complete ebook dedicated to their chemistry, whilst Whitmore wrote an American Chemical Society monograph at the topic in 1921. for this reason, very exact monographs at the topic have seemed. In 1967 "The natural Compounds of Mercury", quantity four within the sequence "Methods of Elemento natural Chemistry" seemed and this used to be in 1974 through Houben Weyl's complete quantity, Band XIII/2b, committed totally to the organometallic compounds of mercury. those books conceal the whole box of organomercury chemistry.
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Additional resources for Organomercury Compounds in Organic Synthesis
Sample text
Preparation of Organomercury Compounds The conversion of alkynes to dialkynylmercurials is a well known reaction which has often been used to help characterize terminal alkynes [733]. In fact, it has been suggested as an analytical method for the determination of alkynes [734]. The reaction is commonly run using alkaline mercuric iodide or cyanide solutions and usually affords excellent yields of organomercurial (Eq. 203) [733]. The versatility of this reaction is illustrated by the 2RC=:CH NoOH K2 H9 I4 .
Organosilanes can also provide a valuable source of organomercurials. Aryltrimethylsilanes are readily cleaved by mercuric acetate in acetic acid (Eq. 106) [330--335]. The relative rates of reaction of a variety of subHgIOAc)2 HOAc frH90AC X (106) stituted arylsilanes and the overall kinetics of the reaction are consistent with an electrophilic aromatic substitution reaction. Ferrocenyltrimethylsilanes 21 II. Preparation of Organomercury Compounds behave similarly [336]. Siloxy- [337] and phenoxysilanes [338, 339] also afford arylmercurials, but the latter reaction reportedly proceeds by an electron transfer process (Eqs.
184) [705, 706]. Recently, mercurated ketenes themselves have 2;=to + 2ROH + HgO cat. Hg{OAcJ2 (184) 49 II. Preparation of Organomercury Compounds been obtained from acetic anhydride or isopropenyl acetate (Eqs. 185, 186) [707]. Mercurous salts provide what is apparently the first stable, isolable organomercury(I) compound. XHg" c=c=o (185) XHg/ XHgHg" (186) c=c=o XHgHg/ The mercuration of an enol [708, 709], or enol silanes [710-715] or phosphates [716] provides a highly convenient route to IX-mercury carbonyl compounds, while enol acetates afford either carbonyl compounds [717-720] or the corresponding acetals [721] (Eqs.