Publication

Gezielte Hydroxylierung von Allylstellungen

Manfred Schlosser
1975
Journal Articles

Abstract

Treatment of a-pinene with Me3COK and BuLi gave intermediate I which was oxidized with H2O2 to give 42% (1S,5R)-myrtenol (II, X = OH) and .apprx.1% (1R,3R,5S)-trans-pinocarveol (III, X = OH). Treatment of I with ethylene oxide gave 25% II(X = CH2CH2OH) and 13% III (X = CH2CH2OH). (E)-MeCH:CHCH2K treated with FB(OMe)2 gave intermediate MeCH:CHCH2B(OMe)2 which was oxidized with H2O2 to give 50% Z-MeCH:CHCH2OH, 2% E-MeCH:CHCH2OH, and 7% H2C:CHCH(OH)Me. Analogously obtained was 58% Z-MeCH:CMeCH2OH. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/704393f7-1b77-4a4e-81f3-9b215aabd635

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Manfred Schlosser
1975
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/704393f7-1b77-4a4e-81f3-9b215aabd635

About this result

Related concepts (10)

Ethylene

Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon double bonds). Ethylene is widely used in the chemical industry, and its worldwide production (over 150 million tonnes in 2016) exceeds that of any other organic compound. Much of this production goes toward polyethylene, a widely used plastic containing polymer chains of ethylene units in various chain lengths.

Ethanol

Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an alcohol, with its formula also written as , or EtOH, where Et stands for ethyl. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive recreational drug, and the active ingredient in alcoholic drinks. Ethanol is naturally produced by the fermentation process of sugars by yeasts or via petrochemical processes such as ethylene hydration.

Persistent carbene

A persistent carbene (also known as stable carbene) is a type of carbene demonstrating particular stability. The best-known examples and by far largest subgroup are the N-heterocyclic carbenes (NHC) (sometimes called Arduengo carbenes), for example diaminocarbenes with the general formula (R2N)2C:, where the four R moieties are typically alkyl and aryl groups. The groups can be linked to give heterocyclic carbenes, such as those derived from imidazole, imidazoline, thiazole or triazole.