Publication

SCOOPY-Reaktionen : Stereoselektivität der Allylalkohol-Synthese via Betain-Ylide

Manfred Schlosser
1971
Journal Articles

Abstract

The stereoselectivity of the SCOOPY reaction, in which allyl alc. derivs. are prepd. by reaction of betaine ylides with carbonyl compds., was investigated by the synthesis of 1-hydroxy-2-octene (I), and 1-hydroxymethyl-2-octene (II) from Ph3P+-CH2 and Ph3P+-CHMe, resp., using HCHO and octanal. Treatment of III with HCHO in the presence of LiBr followed by treatment with n-C5H11CHO gave 10% I having a 97:3 cis-trans ratio. A 36% yield of II with a 30:70 cis-trans ratio was obtained by treating III with n-C5H11CHO and then with HCHO. Treatment of Ph3P+-CHMe with n-C5H11CHO and then with HCHO gave 71% II with a 99.3:0.7 cis-trans ratio, while treatment with HCHO and then with n-C5H11CHO gave 48% II with a 36:64 ratio. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/92f030be-cc29-4388-b84f-fb9ac2e5f91d

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Manfred Schlosser
1971
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/92f030be-cc29-4388-b84f-fb9ac2e5f91d

About this result

Related concepts (12)

Trans fat

Trans fat, also called trans-unsaturated fatty acids, or trans fatty acids, is a type of unsaturated fat that occurs in foods. Trace concentrations of trans fats occur naturally, but large amounts are found in some processed foods. Since consumption of trans fats is unhealthy, artificial trans fats are highly regulated or banned in many nations. However, they are still widely consumed in developing nations, resulting in hundreds of thousands of deaths each year.

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In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food. The term often refers specifically to triglycerides (triple esters of glycerol), that are the main components of vegetable oils and of fatty tissue in animals; or, even more narrowly, to triglycerides that are solid or semisolid at room temperature, thus excluding oils.

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Related publications (1)

SCOOPY-Reaktionen : Stereoselektivität der Allylalkohol-Synthese via Betain-Ylide

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Phosphor-Betaine als Wittig-Zwischenstufen : Es gibt sie doch !