Boron monochloride

Murga, J., Falomir, E., Carda, M., Marco, J. A. An ab initio study of the enolboration of 3-pentanone mediated by boron monochlorides L2BCI. Tetrahedron 200, 57, 6239-6247. 

The iodination reaction can also be conducted with iodine monochloride in the presence of sodium acetate (240) or iodine in the presence of water or methanolic sodium acetate (241). Under these mild conditions functionalized alkenes can be transformed into the corresponding iodides. AppHcation of B-alkyl-9-BBN derivatives in the chlorination and dark bromination reactions allows better utilization of alkyl groups (235,242). An indirect stereoselective procedure for the conversion of alkynes into (H)-1-ha1o-1-alkenes is based on the mercuration reaction of boronic acids followed by in situ bromination or iodination of the intermediate mercuric salts (243). 

Pyridazines form complexes with iodine, iodine monochloride, bromine, nickel(II) ethyl xanthate, iron carbonyls, iron carbonyl and triphenylphosphine, boron trihalides, silver salts, mercury(I) salts, iridium and ruthenium salts, chromium carbonyl and transition metals, and pentammine complexes of osmium(II) and osmium(III) (79ACS(A)125). Pyridazine N- oxide and its methyl and phenyl substituted derivatives form copper complexes (78TL1979). 

Organoborane intermediates can also be used to synthesize alkyl halides. Replacement of boron by iodine is rapid in the presence of base.150 The best yields are obtained with sodium methoxide in methanol.151 If less basic conditions are desirable, the use of iodine monochloride and sodium acetate gives good yields.152 As is the case in hydroboration-oxidation, the regioselectivity of hydroboration-halogenation is opposite to that observed for direct ionic addition of hydrogen halides to alkenes. Terminal alkenes give primary halides. 

Sulphur, selenium and tellurium are soluble in the oxychloride in the cold, but on heating, reaction may take place. Sulphur interacts to form selenium monochloride, sulphur monochloride and sulphur dioxide. Tellurium is converted into its tetrachloride. Both red and yellow phosphorus react violently with the oxychloride, forming phosphorus pentoxide and selenium mono- and tetra-chlorides. Carbon, silicon and boron are unattacked. 

V. Braun reaction Cyanogen bromide. Phosphorus tribromide. Piperidine. Thionyl chloride. Bromination Aluminum bromide. Aluminum chloride. Boron tribromide. Bromine chloride. N-Bromocaprolactam. N-Bromosuccinimide. Bromotrichloromethane. Cupric bromide. Dibenzoyl peroxide. l,3-Dibromo-5,5-diraethylhydantoin. 1,2-Dibromotetrachloromethane. HBr-scavengers acetamide and potassium chlorate. Iodine. Iodine monobromide. Iron. Mercuric acetate. Phenyl trimethylammonium perbromide. Phosphorus trichloride. Pyridine. Pyridine perbromide. Pyridinium hydrobromide perbromide. Silver sulfate. Sodium acetate. Sodium hypobromite. Sulfur. Sulfur monochloride. Tetramethylaramonium tribromide. M-Tribromoacetophenone. Trichloromethane sulfonyl bromide. Trilluoroacetyl hypobromite. Triphenylphosphine dibromide. 

Friedel-Craets reaction Aluminum chloride. Benzenesulfonic anhydride. Boron trifluoride. 7-Butyrolactone. Catechol dichloromethylene ether. Chloroform (solvent). Chloromethyl methyl ether. 1,1-Didilorodimethyl ether. 2,4-Dinitrobenzenesulfenyl chloride. Hydrogen fluoride. Iodine. Folyphosphoric add. Sodium aluminum chloride. Stannic chloride. Sulfur. Sulfur monochloride. Titanium tetrachloride. Trichloramine. Zirconium tetrachloride. Friedel-Craets type reactions Dimethylacetamide. lodosobenzene. 

Pyridazine forms a stable adduct with iodine,751-755 with semiconductor properties.756-758 Similar complexes were prepared from iodine monochloride, bromine,753 and nickel(II) ethyl xanthate.759 Complexes of pyrida-zines with iron carbonyls and with iron carbonyls and triphenylphosphine have been prepared and investigated.760 766 Complexes of pyridazines with boron trihalides,767 silver salts,768 mercury(I) salts,769,770 iridium salts,771-774 ruthenium salts,775,776 and chromium carbonyls are re-... 

Fluorothiiranes are also prepared by cyclization of open-chain precursors. Treatment of sulfenyl chloride 92 with the triethylamine-boron triiluoride complex gave thiirane 30 in 68% yield. Tris(diethylamino)phosphine transformed disulfide 94, prepared from alkene 93 and sulfur monochloride, into thiirane 95. An indirect route from a chlorodisulfide that has the advantage of utilizing both halves of the molecule is exemplified by the transformation of 96 into thiirane 97. ... 

An interesting topological effect is the increased terminal chlorination of fatty acids when they are adsorbed and aligned on alumina Silicon disulfide and particularly boron sulfide have been used with advantage instead of phosphorus pentasulfide to replace carbonyl oxygen by sulfur The addition of sulfur monochloride to olefins followed by reduction of the adduct with sodium sulfide provides a convenient inexpensive route to a large number of episulfides A direct conversion of ar. nitro compounds to isothiocyanates has been reported Sec. phosphines add easily to olefins under UV-irradiation Advances in peptide synthesis include the use of acyloxyphospho-nium salts prepared with hexamethylphosphoramide a simple synthesis with triphenyl phosphite , and the use 4-picolyl esters at the... 

The standard reaction enthalpies are positive, the standard reaction entropies negative the amount of monochloride increases with increasing temperature and decreasing pressure. For a given temperature and pressure the equilibrium shifts to the right as the group is descended from boron to indium. 

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