Solvent-free reactions of N,N′-thiocarbonyldiimidazole with ferrocenylcarbinols |
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Authors: | Douglas Onyancha Vincent Nyamori Christopher Imrie Thomas IA Gerber |
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Institution: | a Department of Chemistry, Nelson Mandela Metropolitan University, P.O. Box 77000, Port Elizabeth 6031, South Africa b School of Chemistry, University of Kwazulu-Natal, Private Bag X 54001, Durban 4000, South Africa |
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Abstract: | The efficient and simple routes for the synthesis of various ferrocenyl derivatives from ferrocenylcarbinols and N,N′-thiocarbonyldiimidazole (TCDI) are described. It involves grinding the two substrates in a Pyrex tube with a glass rod at room temperature. The reaction of ferrocenylmethanol (1a) provided S,S-bis(ferrocenylmethyl)dithiocarbonate (1b), whose crystal structure and a plausible mechanism for its formation are also reported. The reaction of 1-ferrocenyl-1-phenylmethanol (2a) and 1-ferrocenylbutanol (2b) gave the products 2c and 2d, respectively. The reaction of ω-ferrocenyl alcohols 4-ferrocenylphenol (3a) and 6-ferrocenylhexan-1-ol (3b) yielded the products 3c and 3d, respectively. Reaction of 1,1′-ferrocenedimethanol (3e) afforded 3f in moderate yield, and by contrast, it was not similar to 1b. Reaction of 4-(trifluoromethyl)phenyl]methanol (4a) provided the thiocarbonate 4b in good yield. |
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Keywords: | Ferrocenylcarbinols S S-bis(ferrocenylmethyl)dithiocarbonate Solvent-free Thiocarbonylimidazolides |
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