Publication

The Homoconjugated Electron-Releasing Carbonyl Group of 1-Methylbicyclo[2.2.1]Hept-5-En-2-One - Regioselective Syntheses of 5-Chloro-1-Methylbicyclo[2.2.1]Hept-5-En-2-One and 6-Chloro-1-Methylbicyclo[2.2.1]Hept-5-En-2-One

Pierre Vogel
1993
Journal Articles

Abstract

Syntheses of (+/-)-2-exo-cyano-1-methyl-7-oxabicyclo[2.2.1]hept-5-en-2-endo-yl acetate (1) and of (+/-)-1-methyl-7-oxabicyclo[2.2.1]hept-5-en-2-one (2) are reported. The additon of PhSeCl to 1 afforded (+/-)-5-endo-chloro-2-exo-cyano-1-methyl-6-exo-(phenylselenenyl)-7-oxabi cyclo[2.2.1]hept-2-endo-yl acetate (6), whereas 2 added to PhSeCl with the opposite regioselectivity giving (+/-)-6-endo-chloro-1-methyl-5-exo-(phenylselenenyl)-7-oxabicyclo[2.2.1] heptan-2-one (7). These adducts were converted into 5-chloro-1-methyl-7-oxabicyclo[2.2.1]hept-5-en-2-one (9) and 6-chloro-1-methyl-7-oxabicyclo[2.2.1]hept-5-en-2-one (10), respectively.

Official source

https://infoscience.epfl.ch/entities/publication/cd9302c9-c270-4c61-ac43-ff682aefea24

About this result

This page is automatically generated and may contain information that is not correct, complete, up-to-date, or relevant to your search query. The same applies to every other page on this website. Please make sure to verify the information with EPFL's official sources.

Graph Chat

Chat with Graph Search

Ask any question about EPFL courses, lectures, exercises, research, news, etc. or try the example questions below.

DISCLAIMER: The Graph Chatbot is not programmed to provide explicit or categorical answers to your questions. Rather, it transforms your questions into API requests that are distributed across the various IT services officially administered by EPFL. Its purpose is solely to collect and recommend relevant references to content that you can explore to help you answer your questions.

Pierre Vogel
1993
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/cd9302c9-c270-4c61-ac43-ff682aefea24

About this result

Related concepts (4)

Oxymercuration reaction

In organic chemistry, the oxymercuration reaction is an electrophilic addition reaction that transforms an alkene () into a neutral alcohol. In oxymercuration, the alkene reacts with mercuric acetate () in aqueous solution to yield the addition of an acetoxymercury () group and a hydroxy () group across the double bond. Carbocations are not formed in this process and thus rearrangements are not observed. The reaction follows Markovnikov's rule (the hydroxy group will always be added to the more substituted carbon) and it is an anti addition (the two groups will be trans to each other).

Cycloaddition

In organic chemistry, a cycloaddition is a chemical reaction in which "two or more unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity". The resulting reaction is a cyclization reaction. Many but not all cycloadditions are concerted and thus pericyclic. Nonconcerted cycloadditions are not pericyclic. As a class of addition reaction, cycloadditions permit carbon–carbon bond formation without the use of a nucleophile or electrophile.

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).