Topics in Current Chemistry (vol 155) by Armin de Meijere, Tse-Lok Ho, Henning Hopf, Rafael R.

By Armin de Meijere, Tse-Lok Ho, Henning Hopf, Rafael R. Kostikov, Isao Kuwajima, A.P. Molchanov, Eiichi Nakamura

This sequence provides severe studies of the current place and destiny traits in sleek chemical learn. it really is addressed to all study and commercial chemists who desire to retain abreast of advances of their topic.

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R R R R R :~,<:HH X~ZXX Na'NH3-RR ref. Atk,Ar X:CI,Br ref. 28 The former reduction is thought to occur by two single electron transfers (SET) from the metal surface to the cyclopropane derivative providing a halide and cyclopropyl anion initially. The latter is protonated by the solvent thus leading to the monohalogen derivative which can undergo the reduction process for a second time. 2,- l>~c' H "" ~>

Presumably, the vinylcyclopropylidene to cyclopentadiene isomerization is involved again. _. Br N-CMe 3 ref. t18 This process may also be employed for the preparation of specifically ringsubstituted pyrroles [119]. Novel preparative possibilities arise when cyclopropylidene intermediates are generated from functionalized dihalocyclopropanes. Thus Baird has shown that bicyclic ethers may be formed in high yield by an intramolecular insertion from cyclopropyl alkyl ethers [120]. R1 rB ~ r R 3 0 / J ' ~ R 2 CH3Li= R3~ O R2 R1 B Similar processes have been reported for other ethers [121], alcohols [122], amines [123], sulfides [124], and acetats [125].

The two oxygen atoms seem to prevent a competing cyclopropylidene to allene isomerization, at least at the reported reaction temperature of --75 °C [126]. 54 Gem-Dihalocyclopropanesin Organic Synthes~s The preparative versatility of the dibromovinylcyclopropanes is further demonstrated by their oxidation to gem-dibromo-cyclopropylaldehydes, compounds which are difficult to obtain by other routes [127]. R R B B R=H,CH3,~ Over-all, this route allows the conversion of a conjugated diene into a highly reactive building block which may be subjected to further transformations [128].

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