Publication

Optional ortho or alpha hydroxymethylation of alkylarenes

Manfred Schlosser
1991
Journal Articles

Abstract

Treatment of arenes carrying Me or primary alkyl groups, e.g., EtPh, in THF with potassium tert-butoxide activated butyllithium followed by reaction with formaldehyde gives 2-arylalkanols, e.g., PhCHMeCH2OH. In contrast, if prior to the addn. of the electrophile a stoichiometric amt. of magnesium dibromide is added then the regioisomeric 2-alkylbenzyl alcs., e.g., 2-EtC6H4CH2OH, are formed. [on SciFinder (R)]

Official source

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Manfred Schlosser
1991
Journal Articles

Abstract

Official source

Related concepts (10)

Alkyl group

In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula . Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula .

Amine

In chemistry, amines (əˈmi:n,_ˈæmi:n, ˈeɪmiːn) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline.

Tosyl group

In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or Tos) is a univalent functional group with the chemical formula . It consists of a tolyl group, , joined to a sulfonyl group, , with the open valence on sulfur. This group is usually derived from the compound tosyl chloride, (abbreviated TsCl), which forms esters and amides of toluenesulfonic acid, (abbreviated TsOH). The para orientation illustrated (p-toluenesulfonyl) is most common, and by convention tosyl without a prefix refers to the p-toluenesulfonyl group.