One pot synthesis of maleimide and hydantoin by Fe(CO)(5) catalyzed [2+2+1] co-cyclization of acetylene, isocyanate and CO
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Title |
One pot synthesis of maleimide and hydantoin by Fe(CO)(5) catalyzed [2+2+1] co-cyclization of acetylene, isocyanate and CO
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Creator |
MATHUR, P
JOSHI, RK RAI, DK JHA, B MOBIN, SM |
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Subject |
PHOTOCHEMICAL-REACTIONS
CARBON-DIOXIDE PAUSON-KHAND ALKYNES CYCLOADDITION NICKEL PYRIDINES FERROCENYLACETYLENE HETEROCUMULENES POLYMERIZATION |
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Description |
In the presence of a catalytic amount of Fe(CO)(5), terminal acetylenes, isocyanates and CO undergo [2 + 2 + 1] cyclization to form substituted maleimides and hydantoins; when internal alkynes are used, exclusive maleimide formation is observed. While the maleimides can be obtained as the major products, in up to 90% yield, when the reaction is carried out in CO atmosphere, in absence of CO, the hydantoins are formed in up to 87% yield. Formation of maleimides has been shown to occur via the formation of a ferrole intermediate, whereas the hydantoins are proposed to form through successive insertion of isocyanate into the iron-acetylide bond. All compounds were characterized by spectroscopic methods and molecular structures of some compounds were established by single crystal X-ray diffraction method.
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Publisher |
ROYAL SOC CHEMISTRY
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Date |
2014-10-15T15:56:59Z
2014-10-15T15:56:59Z 2012 |
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Type |
Article
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Identifier |
DALTON TRANSACTIONS, 41(16)5045-5054
http://dx.doi.org/10.1039/c2dt11942k http://dspace.library.iitb.ac.in/jspui/handle/100/15210 |
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Language |
en
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