Advances in Physical Organic Chemistry, Vol. 23 - download pdf or read online

By D. Bethell (ed.)

ISBN-10: 0120335239

ISBN-13: 9780120335237

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However, more detailed studies of the reactions between a variety of alkyl halides and trans-[IrCI(CO)(PR,),] has clarified this confused literature. , 1973; Labinger and Osborn, 1980). The contentious studies with trans-2-bromofluorocyclohexane were repeated with trans-[IrCI(CO)(PMe,),[ and the products isolated and purified fied. The correspondingly much improved 19F nmr spectrum (compared to the previous study) now demonstrated that two products were formed. Furthermore, the reaction of cis-2-bromofluorocyclohexane with trans[IrCI(CO)(PMe,),] yielded an identical 19Fspectrum clearly indicating that complete loss of stereochemistry at the carbon atom had occurred.

Scheme 19 . The reaction of [Re(CO),] - with MeC(CH,I), also produces the 1 -methylcyclopropylmethyl-derivative, but [Re,(CO),I] - is also formed in appreciable amounts. In contrast, [Mn(CO),]- reacts with MeC(CH,I), to yield the “carbonyl inserted” acyl-product as shown in (41). Mechanisms have been postulated to rationalise these products but these are highly speculative. 4[Mn(CO),]- + MeC(CH,I), - [Mn,(CO),,]- + (CO),Mn-C + 3113 Activation parameters %I1 (41) Within this section will be discussed the activation parameters ( A H * , AS* and AV*) that have been measured for the reactions between metal nucleophiles and carbon compounds.

The demonstration of free-radical reactions which proceed with inversion of the configuration at carbon (Kuivila and Alnajjar, 1982; Ashby and DePriest, 1982) must cast some doubt on this stereochemical distinction between the two pathways. The reaction of Me&- with 2-butyl bromide has been shown to proceed with inversion of the carbon’s configuration (Jensen and Davis, 1971), but many subsequent stereochemical studies have shown more complicated behaviour. The reactions of Me,Sn- with cis-4-t-butylcyclohexyl bromide and with trans-4-t-butylcyclohexyl tosylate have been shown by H nmr spectroscopy to give the same product, and on the basis of independent evidence this product has been assigned the cis-configuration as shown in Scheme 7.

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Advances in Physical Organic Chemistry, Vol. 23 by D. Bethell (ed.)


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