Propylmagnesium chloride 3-

The presence of bis[2-(A,A-dimethylamino)ethyl]ether allows a selective halogen-magnesium exchange of iodo- and bromoaromatics at ambient temperature using iso-propylmagnesium chloride. Sensitive carboxylic ester and cyano groups are well tolerated (equations 29 and 30). ... 

Unfortunately, the yield depends highly on the concentration of the reaction mixture (Scheme 12). As shown below, in the case of the reaction of 6-bromohexanoyl chloride with propylmagnesium chloride, the yield jumps from 38% to 91% when the concentration decreases from 1.2 M to 0.4 M. It is a drawback for large-scale applications since the concentration cannot be higher than 0.5 M. 

Bromine at C5 was exchanged with lithium using BuLi in THF at -100°C or with magnesium using zso-propylmagnesium chloride in... 

A solution of 13.2 grams of 2-trifluoromethyl-9-xanthenone in tetrahydrofuran is added over 1 hour to 16.0 grams of 3-(4-benzyloxyethyl-l-piperazinyl) propylmagnesium chloride, prepared as above, in tetrahydrofuran while gently... 

The preparation of another (also paramagnetic) dinitrogen complex, [(CsHsVTiJjNjjMgCl (31), was subsequently reported from reaction of iso-propylmagnesium chloride and Or)-C5H5)2TiCl2 with N2 in diethyl ether at -60°C (76). The complex shows an i>N N absorption at 1255 cm-1 (1215 cm-1 with 15N2), which is even lower than that for [(C5H )2Ti]2N2 (30). Elemental analyses and vibrational data were said to be consistent with these proposed structures ... 

Since magnesium becomes bonded to the same carbon that previously held halogen, the alkyl group remains intact during the preparation of the reagent. Thus /1-propyl chloride yields H-propylmagnesium chloride, and isopropyl chloride yields isopropylmagnesium chloride. 

Problem 3.9 (a) Which alkane would you expect to get by the action of water on -propylmagnesium chloride (b) On isopropylmagnesium chloride (c) Answer (a) and (b) for the action of deuterium oxide ( heavy water, D2O). 

Derivation By Grignard reaction of silicon tetrachloride and propylmagnesium chloride. 

Addition of NaCl/H O Derivatisation with 4% NaBEt4 Separation by cryogenic trapping in an U-tube filled with chromatographic material Detection by QFAAS (Lab. 01) Complexation with EDTA and DDTC hexane extraction Derivatisation by addition of 2 mol L" propylmagnesium chloride elution with hexane Separation with U-tube filled with chromatographic material Detection by QFAAS (Lab.02)... 

Supercritical fluid extraction using CO, with methanol liquid-liquid extraction of SFE eluate with n-hexane after complexation with DDTC Derivatisation by addition of propylmagnesium chloride Separation by CGC detection by MS (Lab. 04)... 

As in the case of organoaluminium compounds, unusual stereochemistries can be imposed by suitable design of ligands. Thus, reaction of GaCb with 3,3, 3 -nitrilotris(propylmagnesium chloride), [N (CH2)3MgCl)3], yields colourless... 

Methylmagnesium chloride Methylmagnesium bromide Methylmagnesium iodide Ethylmagnesium bromide Propylmagnesium chloride Isopropylmagnesium... 

Quinoxaline readily reacts with Grignard reagents. Addition of two molecular proportions of allylmagnesium bromide and of 3-(dimethylamino)propylmagnesium chloride, and hydrolysis of the initial adducts, gives the tetrahydroquinoxalines 2 and 3, respectively. The 1 1 adducts 4, 5, and 6 are obtained from the reaction of quinoxaline with diphenylcyclopropenone, diphenylcyclopropenethione, and methyl phenylhydrazonochloroacetate in the presence of triethylamine, respectively. In the latter case the presumed intermediate is the dipolar... 

Secondary aminophosphines are rare, but may be obtained in a straightforward manner, as shown for (57) and (58). The latter are also obtained, together with the tertiary aminophosphines, when (59) are treated with iso-propylmagnesium chloride. [58 R = N(SiMe3)2] has been made independently by Cowley, who also reports (60). Reduction of bis(trimethylsilyl)amino-dichlorophosphine gave either (61) or (62), depending on the amount of lithium aluminium hydride used. Experimental details for the large-scale preparation of (silylamino)phosphines have been published. ... 

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