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A common method for expanding a ring involves opening cyclopropane-containing bicyclic intermediate. 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 ...
An example of such a rearrangement is the shift of substituents on tropilidenes (1,3,5-cycloheptatrienes). When heated, the pi-system goes through an electrocyclic ring closing to form bicycle[4,1,0]heptadiene (norcaradiene). Thereafter follows a [1,5] alkyl shift and an electrocyclic ring opening. norcaradiene rearrangement
In organic chemistry, annulation (from Latin anellus 'little ring'; occasionally annelation) is a chemical reaction in which a new ring is constructed on a molecule. [1] Examples are the Robinson annulation, Danheiser annulation and certain cycloadditions.
Heteroarenes are aromatic compounds, where at least one methine or vinylene (-C= or -CH=CH-) group is replaced by a heteroatom: oxygen, nitrogen, or sulfur. [3] Examples of non-benzene compounds with aromatic properties are furan, a heterocyclic compound with a five-membered ring that includes a single oxygen atom, and pyridine, a heterocyclic compound with a six-membered ring containing one ...
Simple aromatic rings can be heterocyclic if they contain non-carbon ring atoms, for example, oxygen, nitrogen, or sulfur. They can be monocyclic as in benzene, bicyclic as in naphthalene, or polycyclic as in anthracene. Simple monocyclic aromatic rings are usually five-membered rings like pyrrole or six-membered rings like pyridine.
In commercial applications, the alkylating agents are generally alkenes, some of the largest scale reactions practiced in industry.Such alkylations are of major industrial importance, e.g. for the production of ethylbenzene, the precursor to polystyrene, from benzene and ethylene and for the production of cumene from benzene and propene in cumene process:
The fluorine atom is para with respect to the substituent Z in the benzene ring. The image on the right shows four distinguished ring carbon atoms, C1, C2, C3, C4 in p-F-C 6 H 4-Z molecule. The carbon with Z is defined as C1(ipso) and fluorinated carbon as C4(para). This definition is followed even for Z = H.
The Buchner ring expansion reaction was first used in 1885 by Eduard Buchner and Theodor Curtius [1] [2] who prepared a carbene from ethyl diazoacetate for addition to benzene using both thermal and photochemical pathways in the synthesis of cycloheptatriene derivatives. The resulting product was a mixture of four isomeric carboxylic acids ...