Pentane 2-iodo

Vicinal iodo carboxylates may also be prepared from the reaction of olefins either with iodine and potassium iodate in acetic acid/ or with N-iodosuccinimide and a carboxylic acid in chloroform. " A number of new procedures for effecting the hydroxylation or acyloxylation of olefins in a manner similar to the Prevost or Woodward-Prevost reactions include the following iodo acetoxylation with iodine and potassium chlorate in acetic acid followed by acetolysis with potassium acetate reaction with iV-bromoacetamide and silver acetate in acetic acid reaction with thallium(III) acetate in acetic acid and reaction with iodine tris(trifluoroacetate) in pentane. ... 

This material is recrystallized from diethyl ether/pentane (2 1) to give 15.1 g (69%) of 2-iodo-2-cyclohexen-1-one as a pale yellow solid, mp 48.5-49°C (Note 7). If desired, an additional 2.4 g (11% mp 48-49°C) can be isolated by concentration of the mother liquor, column chromatography of the residue on 40 g of silica gel eluting with a mixture of 10% ethyl acetate in petroleum ether, and recrystallization of the collected iodoenone from pentane. 

A 100-mL flask protected with a positive pressure of nitrogen is charged with 11 mmol of a 0.25 M pentane solution of iodo(diisopinocampheyl)borane [derived from ( +)-a-pinene]. The solution is cooled to — 100 C and treated dropwise with a solution of 980 mg (10 mmol) of 1,2-epoxycyclohexane in 2 mL of pentane. After stirring the solution for 0.5 h at —100 CC, the mixture is quenched by the addition of 1.8 mL (excess) of butanal. The mixture is allowed to warm gradually to r.t. and stirred for an additional 1 h. By that time "B NMR indicates clean formation of boronate [R OB(OEt)Ipc, d = 31], The mixture is diluted with 50 mL of pentane and treated with a 4 M THF solution of 12 mmol of 2.2 -diethanolamine. After the solution is stirred for 0.5 h, the precipitated boronate 2,2 -diethanolamine complex is filtered off and the filtrate is washed with water and brine and dried with anhyd Na2S04. The solution is concentrated under reduced pressure and the residue is purified by column chromatography followed by crystallization from pentane to provide the title compound in 89% yield mp 44 - 45°C [a] 3 —31.6 (c = 5, CHClj). 

Fig. 6 Temperature dependence of koBs values for para-fluoro (1), para-chloro (2), para-bromo (3), and para-iodo (4) singlet phenylnitrene in pentane.

As can be seen, the isolation of l-halobicyclo[l.l.l]pentanes offered an opportunity for further molecular manipulation. To illustrate this, the adduct generated from 3-iodo-4,5-dihy-drofuran-2(3//)-one and [1.1.IJpropellane was reacted with tributyltin hydride in the presence of the radical trapping agent methyl acrylate to afford the 1,3-disubstituted biey-clo[l.l.l]pentane 27 in a total yield of 39%.43... 

Pentane 3-Chloro-1-iodo-oclalluo-ro-2H.2H- E10b2. 98 (bduct)... 

Preparation 315.—jS-Iodopropionic Acid [Z-Iodo-pentan acid],... 

A further novel method for demetallation provides even higher yields. Hieber-type reaction of the tricarbonyl(ri4-cydopentadienone)iron complex with sodium hydroxide to the corresponding hydride complex followed by ligand exchange with iodo-pentane affords an intermediate iodoiron complex, which is readily demetallated in the presence of air and daylight at room temperature (Scheme 1.4) [9]. Combining steps a-c in a one-pot procedure without isolation of the intermediate hydride complex gave yields of up to 98%. 

An important modification is reaction of p-dicarbonyl compounds with [hydrox y(tosyloxy)iodo]benzene and selenourea as a one-pot synthesis [177], Similarly, a-tosyloxylation of acetophenones, cyclohexanone, or pentan-3-one with the same reagent, followed by treatment with arylselenobenzamides, gives 2,4-disubstituted and 2,4,5-trisubstituted 1,3-selenazoles [178],... 

C6H1202 4-methylpentanoic acid 646-07-1 240.15 15.979 2 8727 C6H13I 1 -iodo-2-methyl pentane 31294-94-7 199.94 12.179 2... 

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