Olefins guanidines

Chemical name l-(6-Chloropyridin-3-ylmethyl)-2-iminoimidazolidine Common name Olefinic guanidine /... 

Grignard reagent in the preparation of a hydrocarbon, 4, jg Grignard reagent to olefins, 6, 32 Guaiacol, 3, 28 Guanidine, 7, 69... 

Bicychc pyrazinones foimd in several natural products were synthesized via Michael addition of heterocyclic amines to nitro olefin followed by reduction/cyclization of the nitro group of the adduct [20] (Scheme 5). Further elaboration of the C-6 methoxycarbonyl group in pyrazinone to the n-propyl guanidine group could result in the synthesis of indoloperamine. 

Regulatory position Regulated metabolites in groundwater include the parent, urea, guanidine and guanidine olefin metabolites. The drinking water health advisory level (HAL) is 399 M.g L T... 

FD-MS is also an effective analytical method for direct analysis of many rubber and plastic additives. Lattimer and Welch [113,114] showed that FD-MS gives excellent molecular ion spectra for a variety of polymer additives, including rubber accelerators (dithiocar-bamates, guanidines, benzothiazyl, and thiuram derivatives), antioxidants (hindered phenols, aromatic amines), p-phcnylenediamine-based antiozonants, processing oils and phthalate plasticisers. Alkylphenol ethoxylate surfactants have been characterised by FD-MS [115]. Jack-son et al. [116] analysed some plastic additives (hindered phenol AOs and benzotriazole UVA) by FD-MS. Reaction products of a p-phenylenediaminc antiozonant and d.v-9-lricoscnc (a model olefin) were assessed by FD-MS [117],... 

Terada and co-workers reported a novel guanidine catalyst with a chiral binaphthol backbone for the asymmetric addition of dicarbonyl compounds to nitro-olefins [126]. Substitution on the binaphthol backbone dramatically increased enantioselectivity. 

Cyanogen Iodide (ICN) has been used extensively for the cyanation of alkenes and aromatic compounds [12], iodination of aromatic compounds [13], formation of disulfide bonds in peptides [14], conversion of dithioacetals to cyanothioacetals [15], formation of trans-olefins from dialkylvinylboranes [16], lactonization of alkene esters [17], formation of guanidines [18], lactamization [19], formation of a-thioethter nitriles [20], iodocyanation of alkenes [21], conversion of alkynes to alkyl-iodo alkenes [22], cyanation/iodination of P-diketones [23], and formation of alkynyl iodides [24]. The products obtained from the reaction of ICN with MFA in refluxing chloroform were rrans-16-iodo-17-cyanomarcfortine A (14)... 

Resins carrying the guanidine function have been patented as catalyst[128] for the preparation of organic disulfides and polysulfides11291 and the preparation of sulfonated olefins.[130]... 

Figure 5 Imidacloprid metabolites in rats, insects and plants. I - 6-chloronicotinic acid (mammalian route of elimination) rosoimine III - 4-hydroxy IV - 5-hydroxy V - guanidine VI - urea VII - olefin VIII - 4,5-dihydroxy derivatives.

Olefin Polymerization Reactions Catalyzed by Lanthanide Amidinates and Guanidinates... 

The structure of arenaine (84) was revealed from the interpretation of its n.m.r. ( H and C) spectra. Examination of the C noise resonance decoupled and single frequency decoupled spectra showed the presence of three non-proto-nated carbons (carbonyl, guanidine, and a-amino-tetrahedral types), three methine (olefinic methine, aminomethine, and one other) carbons, three methylenes (one olefinic and two saturated ones which appear at highly shielded and deshielded positions, thus implying that they are part of a R3CCH2CH2 unit), and two methyl groups. This information alone allows formulation of the... 

A guanidine base has also been used for intramolecular HWE reaction. Nicolaou et al. reported a synthetic study of the originally proposed structure of diazonamide A (74) [19], employing the modified Masamune-Roush conditions [18]. Thus, reaction of aldehyde 72 with TMG (3)-LiCl in DMF at 70 °C generated 73 as a single atropisomer in 55-60% yield. Under other reaction conditions, for example, LHMDS in THE or DBU-LiCl in acetonitrile, 73 was obtained in only 0 35% yield (Scheme 7.15). Unfortunately, this advanced intermediate could not be transformed to the final product 74, because the C29-30 olefin was resistant to oxidation. 

These bases have in recent years been utilized as stoichiometric bases in Wittig reactions [23], in Horner-Wadsworth olefinations [23] and in the synthesis of etioporphyrin from protoporphyrin [24]. Guanidines are useful as catalysts in, for example, the selective synthesis of monoglycerides [25], enone epoxidation... 

Feng and coworkers reported a highly enantioselective Michael reaction of p-ketoesters and nitro-olefins. Ethyl acetate, the recommended solvent, (Table 23.1), is rarely employed in guanidine catalysed asymmetric reactions. It was found to be optimal for this reaction and 2 to 5 mol% of catalyst gives excellent enantioselectivity and diastereoselectivity. The yields are generally high and a practical application of the reaction was demonstrated with a 2-g-scale synthesis of an intermediate for the synthesis of Ramipril analogues (Scheme 23.8). 

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