Publication

Synthesis of 1,1-Bis(3,5-Dimethyl-2-Furyl)Ethene - the Chemo-Selectivity and Site-Selectivity of Its Cycloadditions

Pierre Vogel
1993
Journal Articles

Abstract

The new polyene 1,1-bis(3,5-dimethyl-2-furyl)ethene (11) was derived from 2,4-dimethylfuran. Its reaction with dienophiles such as maleic anhydride, benzoquinone or 1-cyanovinyl acetate generated exclusively Diels-Alder adducts (9-oxabicyclo[4.3.0]nona-1,7-diene derivatives) involving the exocyclic double bond and one double bond of one furyl unit. The reaction of 11 with didehydrobenzene (benzyne) gave a 7-oxabicyclo[2.2.1]hepta-2,5-diene derivative resulting from the exclusive Diels-Alder addition of one furyl group, whereas dimethyl acetylenedicarboxylate added to 11 giving a mixture of the corresponding 7-oxabicyclo[2.2.1]hepta-2,5-diene and 9-oxabicyclo[4.3.0]nona-1,4,7-triene derivatives. With allenic acid, 11 added in a [2+2] fashion exclusively with its exocyclic double bond giving 2-[3,3-bis(3,5-dimethyl-2-furyl)cyclobutylidene]acetic acid with high selectivity.

Official source

https://infoscience.epfl.ch/entities/publication/fec372f7-4807-4afc-a001-1908626a12a3

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Pierre Vogel
1993
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/fec372f7-4807-4afc-a001-1908626a12a3

About this result

Related concepts (17)

1,3-Dipolar cycloaddition

The 1,3-dipolar cycloaddition is a chemical reaction between a 1,3-dipole and a dipolarophile to form a five-membered ring. The earliest 1,3-dipolar cycloadditions were described in the late 19th century to the early 20th century, following the discovery of 1,3-dipoles. Mechanistic investigation and synthetic application were established in the 1960s, primarily through the work of Rolf Huisgen. Hence, the reaction is sometimes referred to as the Huisgen cycloaddition (this term is often used to specifically describe the 1,3-dipolar cycloaddition between an organic azide and an alkyne to generate 1,2,3-triazole).

Double bond

In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist between two different elements: for example, in a carbonyl group between a carbon atom and an oxygen atom. Other common double bonds are found in azo compounds (N=N), imines (C=N), and sulfoxides (S=O).

Diene

In organic chemistry, a diene (ˈdaɪiːn ); also diolefin, daɪˈoʊləfᵻn ) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alkene units, with the standard prefix di of systematic nomenclature. As a subunit of more complex molecules, dienes occur in naturally occurring and synthetic chemicals and are used in organic synthesis. Conjugated dienes are widely used as monomers in the polymer industry. Polyunsaturated fats are of interest to nutrition.