| abstract |
A process for the preparation of an oxirane, aziridine or cyclopropane of formula (I) wherein, X is oxygen, NR 4 or CHR 5 ; R 1 is hydrogen, alkyl, aryl, heteroaromatic, heterocyclic or cycloalkyl; R 2 is hydrogen, alkyl, aryl, heteroaromatic, CO 2 R 8 , CHR 14 NHR 13 , heterocyclic or cycloalkyl; or R 1 and R 2 join together to form a cycloalkyl ring; R 3 is hydrogen, alkyl, aryl, heteroaromatic, CO 2 R 8 , R 8 3 Sn, CONR 8 R 9 or trimethylsilyl; R 4 and R 5 are, independently, alkyl, cycloalkyl, aryl, heteroaromatic, SO 2 R 8 , SO 3 R 8 , COR 8 , CO 2 R 8 , CONR 8 R 9 or CN, or R 4 can also be P(O)(aryl) 2 ; R 8 and R 9 are independently alkyl, aryl or arylalkyl; R 13 and R 14 are independently hydrogen, alkyl or aryl; the process comprising reacting a mixture of a compound of formula (II), wherein R 1 , R 2 and X are as defined above, and a sulphide of formula SR 6 R 7 , wherein R 6 and R 7 are independently alkyl, aryl or heteroaomatic, or R 6 and R 7 join together to form a cycloalkyl ring which optionally includes an additional heteroatom, with either (i) a metallocarbon obtainable by reacting an alkylmetal with a methane derivative of formula CHR 3 X'X", wherein R 3 is as defined above, and X' and X" are independently, a leaving group, or (ii) a metallocarbon obtainable by reacting a compound of formula (III), (wherein R 3 may not be hydrogen) with a suitable organometallic or inorganic reagent. |