Publication

Stereoisomer-uniform olefins

Manfred Schlosser
1968
Patents

Abstract

Homogeneous stereoisomeric olefins of the general formula I (R1 and R2 = alkyl, R3 = H and(or) alkyl) were prepd. by reacting a phosphorus ylide (general formula Ar3P+:C-HR) and a carbonyl compd. R2COR3 with stoichiometric amt. of a strong base, followed by addn. of a proton donor to convert the intermediate product into an olefin and triarylphosphine oxide. In a sample, the phosphorus ylide was prepd. by reacting Ph3P+EtCl- with PhLi (1 mole) in a mixt. of ether 3 and tetrahydrofuran 1 part at 0 Deg. The phosphorus ylide was reacted with 1 mole BzH, and the resulting betaine type intermediate was then reacted at -20 Deg with 1 mole PhLi. After .apprx.30 min. the mixt. was dild. with 2 moles tert-BuOH and afterthe addn. of 1.5 moles KOBu-tert stirred at 25 Deg for 1.5 hrs. b-Methylstyrene was isolated in 69% yield having trans to cis ratio 99:1. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/14ed72eb-0d15-4adc-86c7-13fc4511137d

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Manfred Schlosser
1968
Patents

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/14ed72eb-0d15-4adc-86c7-13fc4511137d

About this result

Related concepts (30)

Ylide

An ylide or ylid (ˈɪlɪd) is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both atoms have full octets of electrons. The result can be viewed as a structure in which two adjacent atoms are connected by both a covalent and an ionic bond; normally written X+–Y−. Ylides are thus 1,2-dipolar compounds, and a subclass of zwitterions.

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 .

Chemical formula

In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as parentheses, dashes, brackets, commas and plus (+) and minus (−) signs. These are limited to a single typographic line of symbols, which may include subscripts and superscripts. A chemical formula is not a chemical name since it does not contain any words.