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The Buchner ring expansion is a two-step organic C-C bond forming reaction used to access 7-membered rings. The first step involves formation of a carbene from ethyl diazoacetate , which cyclopropanates an aromatic ring.
The strategy can start with a Simmons-Smith-like cyclopropanation of a cyclic alkene. [8] A related cyclopropane-based ring expansion is the Buchner ring expansion. The Buchner ring expansion is used to convert arenes to cycloheptatrienes. The Buchner ring expansion is encouraged to open to the desired product by placing electron withdrawing ...
The Buchner–Curtius–Schlotterbeck reaction is the reaction of aldehydes or ketones with aliphatic diazoalkanes to form homologated ketones. [1] It was first described by Eduard Buchner and Theodor Curtius in 1885 [ 2 ] and later by Fritz Schlotterbeck in 1907. [ 3 ]
Carbenes had first been postulated by Eduard Buchner in 1903 in cyclopropanation studies of ethyl diazoacetate with toluene. [29] In 1912 Hermann Staudinger [30] also converted alkenes to cyclopropanes with diazomethane and CH 2 as an intermediate. Doering in 1954 demonstrated their synthetic utility with dichlorocarbene. [31]
Cyclopropanation is also stereospecific as the addition of carbene and carbenoids to alkenes is a form of a cheletropic reaction, with the addition taking place in a syn manner. For example, dibromocarbene and cis -2-butene yield cis -2,3-dimethyl-1,1-dibromocyclopropane, whereas the trans isomer exclusively yields the trans cyclopropane.
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Definitive mechanistic studies of rhodium-catalyzed cyclopropanation are lacking. However, the mechanism has been rationalized based on product distribution and stereoselectivity. [4] Attack of the diazo compound on the metal center generates a zwitterionic metal alkyl complex, which expels nitrogen gas to afford a metal carbene intermediate.
The term has evolved since its first recorded use in American writer Henry David Thoreau’s book "Walden" which reports his experiences of living a simple lifestyle in the natural world, Oxford ...