Stereoisomer-uniform olefins

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)]


Year:
1968
Publisher:
(Badische Anilin- & Soda-Fabrik AG).
Keywords:
Note:
CAN 69:86586
25
Noncondensed Aromatic Compounds
Patent
written in German.
19680620
103-30-0P; 768-00-3P; 873-66-5P; 1005-64-7P; 6111-82-6P; 13389-42-9P; 14850-23-8P; 15192-80-0P Role: IMF (Industrial manufacture), PREP (Preparation) (manuf. of)
Patent number(s):
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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