Publication

About the stereoelectronics of the intramolecular addition of allylsilanes to aldehydes

Manfred Schlosser
2001
Journal Articles

Abstract

(Z)-omega-Trimethylsilyl-(omega-2)-alken-1-ols are readily accessible by consecutive superbase metalation and silylation of (omega-1)-alken-1-ols. These versatile intermediates may be oxidized to give the corresponding (Z)-omega-trimethylsilyl-(omega-2)-alkenals which, in the presence of trifluoroacetic acid, can be converted into 2-vinylcycloalkanols such as 2-vinylcyclohexanol (2), isopulegol (4), and bis(2-vinylcyclobutyl) ether (8). The stereochemical outcome of these cyclization reactions suggests the interference of a novel electrodynamic effect. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/e9da3626-6e0f-4d2a-9980-6c06bfe0e278

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.

Manfred Schlosser
2001
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/e9da3626-6e0f-4d2a-9980-6c06bfe0e278

About this result

Related concepts (19)

Ether

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl or aryl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers.

Aldehyde

In organic chemistry, an aldehyde (ˈældᵻhaɪd) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology. Aldehyde molecules have a central carbon atom that is connected by a double bond to oxygen, a single bond to hydrogen and another single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen.

Diethyl ether

Diethyl ether, or simply ether, is an organic compound in the ether class with the formula or , sometimes abbreviated as . It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It is commonly used as a solvent in laboratories and as a starting fluid for some engines. It was formerly used as a general anesthetic, until non-flammable drugs were developed, such as halothane. It has been used as a recreational drug to cause intoxication.

Related publications (1)

About the stereoelectronics of the intramolecular addition of allylsilanes to aldehydes

Chat with Graph Search

A homologous series of O- and N-functionalized 2,2-difluoro-1,3-benzodioxoles: An exercise in organometallic methodology