N Propyl isocyanide

Fig. 30. Effects of alkyl isocyanides (n-series) on the 600-MHz ring-current-shifted proton resonances of isolated a and p chains of Hb A, Hb A, and sperm whale myoglobin (Mb) in 0.2 M phosphate in D20 at pH 6.6 and 21°C CO, carbon monoxide MNC, methyl isocyanide ENC, ethyl isocyanide nPNC, n-propyl isocyanide nBNC, n-butyl isocyanide. [Adapted from Mims el al. (1983a)].

Fig. 31. A comparison of the 1H chemical shifts for the E11 valine 72-CH3 protons of the various isonitrile complexes of isolated a chains (o) and p chains (A) of Hb A, the o ( ) and p ( ) chains as identified within an intact Hb A molecule, and sperm whale myoglobin ( ). Ligands CO, carbon monoxide M, methyl isocyanide E, ethyl isocyanide P, n-propyl isocyanide B, n-butyl isocyanide iP, isopropyl isocyanide and tB, tert-butyl isocyanide. [From Mims et al. (1983a)].

The reaction is carried out in a 3-1. three-necked flask equipped with a mechanical stirrer, pressure-equalized dropping funnel, reflux condenser, and a nitrogen inlet. In the flask is dissolved 212 g. (1.73 mole) of sublimed decaboranej in 11. of dry benzene. In the dropping funnel is placed 160 g. (2.31 mole) of n-propyl isocyanide, t An ice bath is placed around the flask, and the n-propyl isocyanide is added with stirring over a 4-hour period. The initial colorless solution will develop a deep red-purple color, and then a white solid will separate from solution. After the addition period, the ice bath is removed, the mixture is stirred for another hour, and then allowed to stand for an hour. The solid is isolated by filtration, washed with 800 ml. of ben-... 

This reaction should be done in a well-ventilated hood, t The decaborane is purified by sublimation at 60° and lO" mm. t The n-propyl isocyanide is prepared by the method of Jackson and McKusick/ using 490 g. (2.S mole) of n-propyl iodide and 454 g. (3.3 mole) of silver cyanide. It is observed that, after a long induction period, the reaction becomes quite violent. It is suggested that one half of the propyl iodide be added initially and the other half be added drop by drop over a 2-hour period. The drj- product is used without the final fractional distillation indicated in the reference. 

A soln. of n-propyl isocyanide in petroleum ether (b. p. 40-60°) refluxed 4 days with black Se in a Ng-stream, more Se added, and refluxing continued several days n-propyl isoselenocyanate. Y 70-80%. F. e. s. W. J. Franklin and R. L. Werner, Tetrah. Let. 1965, 3003. 

Many acrylic copolymers are currently used in the textile industry as binders for nonwoven fabrics. The purpose of these fibers is to stabilize the material. In many instances, these copolymers are used in conjunction with amino resins. Casanovas and Rovira have done a study of methyl methacrylate-ethyl acrylate-N-methylol-acrylamide by PY/GC-MS. Among the products identified were methane, ethylene, propene, isobutene, methanol, propionaldehyde, ethanol, ethyl acetate, methyl acrylate, methyl isobutyrate, ethyl acrylate, methyl methacrylate, n-propyl acrylate, and ethyl methacrylate. In this sample, clearly monomer reversion is the primary degradation process occurring however, several other degradation mechanisms are at work. When the sample contains an amino resin in the mixture, acrylonitrile is observed in the pyrogram. Another effect of the amino presence was a marked increase in the amount of methanol detected. Other products detected were meth-oxyhydrazine, methyl isocyanate, and methyl isocyanide. 

Photoextrusion of isocyanides from monoimines (705 R = Ph, cyclohexyl, or n-propyl) has been observed on irradiation in furan. No reaction occurs when cyclohexane is used as solvent. The ketone (706) is formally an adduct of furan with tetramethylcyclopropanone or its derived 1,3-dipoIe (c/ the formal reversal of this in the synthesis of iminocyclobutanones, p.73). 

Polymeric complexes are formed when copper(I) cyanide reacts with ammonia or alkyl and aryl isocyanides. The ammine complex consists of Cu-C-N-Cu-C helices linked by metal-metal bonds to form sheets. The NH3 ligands bond normal to the copper atoms and interlock with NH3 protrusions of other sheets (94). Complex CuCN(Bu"NC) is polymeric (272), and the ethyl, propyl, and 2-butyl isocyanide complexes are also known (139). 

DMSA dimercaptosuccinic acid, EDTA ethylenediaminetetraacetic acid, HMPAO hexamethyl propyl-eneamine oxime, DADS J yM-bis(mercaptoacetyl)ethylenediamine, DADT diaminodithiol, ECD ethylcysteinate dimer, MAG3 mercaptoacetyltriglycine, NOEt Et(OEt)NCS2, DTPA diethylene triamine pentaacetate, MDP methylenediphosphonate, HIDA N-(2,6-dimethylphenylcarbamoylmethyl) iminodiacetic acid, DMPE l,2-bis(dimethylphosphino) ethane, BATO boronic acid technetium oxime, MIBI methoxyisobutyl isocyanide... 

---