Biomaterial Database

One-pot synthesis of alpha-iodo-substituted alpha,beta-unsaturated aldehydes from propargylic alcohols. 2007

Shufeng Chen, and Jianbo Wang

Beijing National Laboratory of Molecular Sciences (BNLMS), Green Chemistry Center (GCC), and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.

An efficient one-pot method for the preparation of alpha-iodo-substituted alpha,beta-unsaturated aldehydes (alpha-iodoenals) from propargylic alcohol is developed. The reaction proceeds via an iodoallene intermediate, which is generated in situ by the reaction of propargylic alcohol with aqueous HI. The iodoallene intermediate is further transformed to an alpha-iodoenal derivative in good overall yield by oxidation with molecular O(2).

UI	MeSH Term	Description	Entries
D007211	Indoles	Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
D010084	Oxidation-Reduction	A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471).	Redox,Oxidation Reduction
D000447	Aldehydes	Organic compounds containing a carbonyl group in the form -CHO.	Aldehyde
D000466	Alkadienes	Acyclic branched or unbranched hydrocarbons having two carbon-carbon double bonds.	Diolefins,Pentadienes
D000478	Alkylation	The covalent bonding of an alkyl group to an organic compound. It can occur by a simple addition reaction or by substitution of another functional group.	Alkylations
D000480	Alkynes	Hydrocarbons with at least one triple bond in the linear portion, of the general formula Cn-H2n-2.	Acetylenic Compounds,Alkyne,Acetylenes
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular
D017605	Bromine Compounds	Inorganic compounds that contain bromine as an integral part of the molecule.	Compounds, Bromine
D020005	Propanols	Isomeric forms and derivatives of PROPANOL (C3H7OH).	Alcohols, Propyl,Propyl Alcohols