Patai S., Rappoport Z. 1996 The chemistry of functional groups. The chemistry of amino, nitroso, nitro and related groups / 0533 626

(R D piperidin-1-yl), respectively. Under similar conditions, the same ester reacts with sodium benzenesulphinate to give a 95:5 mixture of the kinetic product 420 (R D O2SPh) and the thermodynamic product 421 (R D O2SPh)452.

The carbanion derived from dimethyl malonate reacts with the cyclic nitro compounds 422 of ring size 5, 6, 7, 8 and 12 to afford the corresponding esters 423. Acyclic allylic nitro compounds 424 (R D Me, CH2OAc or CO2Et) are attacked by bulky nucleophiles, such as dimethyl malonate anion, mainly at the terminal primary carbon atom to give rearranged products 425, whereas smaller nucleophiles, e.g. the anion derived from methyl cyanoacetate, react at the tertiary carbon atom to yield 426409a,453 455.

Another example of the formation of a rearranged product is the palladium(0)-catalysed reaction of the enolate ion of 2-methylcyclohexanone with 3-methyl-3-nitro-1-butene (equation 138)456.

3-Methyl-3-nitro-1-nonene (427) and sodium phenylthiolate show different modes of behaviour under different conditions: in HMPA the product 428 of attack at the less hindered carbon atom is obtained, whereas in the presence of Pd(PPh3)4 the isomer 429 is produced457.

The allylic nitroalkenes 430 [R1 D R2 D Me; R1 D Me, R2 D CO2Et; R1R2 D CH2 4] react with lithium dialkylcuprates R32CuLi (R3 D Bu or Ph), obtained from organolithium compounds and copper(I) iodide, to yield the rearranged olefins 431458.

Under basic conditions, ˛-nitroalkenes function as synthetic equivalents of allylic nitro compounds; 3-nitro-3-hexene, for instance, reacts with piperidine in the presence of Pd(PPh3)4, to give 2-piperidinyl-3-hexene (equation 139)459.

The two-fold Michael addition of nitroethane to methyl propiolate in the presence of potassium fluoride and the phase-transfer catalyst tetrabutylammonium chloride leads to the diester 432. Treatment of nitroethane with methyl propiolate under these conditions, followed by methyl vinyl ketone, leads to the ‘mixed’ adduct 433460.

NO2

(433)

Oximes RCHDNOH are produced in the reduction of nitroalkanes RCH2NO2 by carbon disulphide in the presence of triethylamine461 or wet potassium carbonate and

a phase-transfer agent462. Best yields are obtained from allylic nitro compounds and arylnitromethanes. When further carbon disulphide and aqueous sodium hydroxide are added, nitriles RCN result463. Conjugated nitroalkenes are reduced by sodium borohydride in methanol/THF to saturated nitro compounds, e.g. PhCHDCHNO2 ! PhCH2CH2NO2, while BH3 Ð THF, generated from sodium borohydride and boron trifluoride etherate in THF, affords the hydroxylamine PhCH2CH2NHOH464.

The ˇ, -epoxy nitro derivatives 435, prepared by oxidation of allylic nitro compounds, e.g. 434, with 3-chloroperbenzoic acid, undergo ring-opening on treatment with triethylamine in wet acetonitrile to yield the nitrovinyl alcohols 436, which arrange to the allylic nitro alcohols 437 on heating. In contrast, reaction of the epoxides with the soft nucleophiles piperidine or sodium benzenesulphinate in the presence of palladium tetrakis(triphenylphosphine) results in ring-scission and replacement of the nitro group to give compounds 438465.

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