By A. Furstner
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Extra resources for Active Metals [chemistry]
Example text
Aryl halides form arylcopper compounds at 25 "C or lower. Arylcopper compounds also undergo epoxide-opening reactions with 1,2-epoxybutane to form a single regioisomer in good yield at room temperature or with moderate heating. Molecules containing both an epoxide and a nucleophile which can undergo an intramolecular cyclization are synthetically useful and have increasingly been reportcd [77]. Epoxyalkylcopper species, using trialkylphosphine-based copper, are able to undcrgo intramolecular cyclization via an epoxide-opening process upon warming, thereby generating new carbocycles.
82: 88: 58: 92: 100: 87: 83: 89: 82: 87: 61 63 29 25 5 80 53 63 59 56 86 85 74 68 96 86 53 79 THF THF THF THF THF THF 0-n 0-rt O-trt 0 0 0 0 0 0 0 0 18 12 42 8 0 13 17 11 18 13 loo: 0 100: 0 loo: 0 100: 0 loo: 0 84: 16 0 : 100 100: 0 Baldwin's rules [78]. Em-mode ring formations are favored in medium size ring cyclizations when both termini of the epoxide are equally substituted. For a shorter connecting chain, such as four-carbon bromoepoxides, reactions always prefer the em-mode ring closures.
Table 1-27 shows the results of reacting various functionalized organocopper reagents, produced from both alkyl and aryl bromides, with benzoyl chloride to form the corrcsponding functionalized ketone products, which were obtained in good isolated yields. Chloride, nitrile, and ester functionalities can be incorporated into the organocopper reagent, but if the functional group is proximal to the carbon-bromine bond the yields are lower. The essential addition of TMSCl to organocopper reagents made from CuCN .
