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  4. w-Hydroxyalkylphosphonium salts as "instant-ylide" components: extremely convenient and highly cis-selective synthesis of alkenol-type pheromones
 
research article

w-Hydroxyalkylphosphonium salts as "instant-ylide" components: extremely convenient and highly cis-selective synthesis of alkenol-type pheromones

Schaub, Bruno
•
Blaser, Gottfried
•
Schlosser, M.  
1985
Tetrahedron Letters

(Z)-Me(CH2)mCH:CH(CH2)nOH (m = 3,4, 6-9; n = 5-12) were prepd. in 69-84% yield by treating Me(CH2)nCHO with Ph3P:CH(CH2)nONa, formed in situ by treating mixts. of Ph3P+CH2(CH2)nOH Br- with paraffin- or butadiene-styrene-divinylbenzene copolymer-coated NaNH2 with THF. [on SciFinder (R)]

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Type
research article
DOI
10.1016/S0040-4039(01)80804-2
Author(s)
Schaub, Bruno
•
Blaser, Gottfried
•
Schlosser, M.  
Date Issued

1985

Publisher

Elsevier

Published in
Tetrahedron Letters
Volume

26

Issue

3

Start page

307

End page

310

Subjects

Pheromones Role: RCT (Reactant)

•

RACT (Reactant or reagent) (cis-alkenols

•

stereoselective synthesis of); Ylides Role: RCT (Reactant)

•

RACT (Reactant or reagent) (phosphorus

•

in situ formation of

•

from hydroxyalkylphosphonium bromide and coated sodium a

•

hydroxyalkylphosphorane prepn aldehyde Wittig; alkenol cis

Note

CAN 103:6067

26-2

Biomolecules and Their Synthetic Analogs

Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.

Journal

written in English.

110-62-3; 111-71-7; 112-31-2; 123-72-8; 124-13-0; 124-19-6 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with hydroxyalkylidenephosphoranes); 85160-80-1; 96854-04-5; 96854-05-6; 96854-06-7; 96854-07-8; 96854-08-9; 96854-09-0; 96854-10-3 Role: RCT (Reactant), RACT (Reactant or reagent) (in situ formation and Wittig reactions of); 85160-81-2P; 96854-11-4P; 96854-12-5P; 96854-13-6P; 96854-14-7P; 96854-15-8P; 96854-16-9P; 96854-17-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 24880-48-6P; 40642-38-4P; 40642-40-8P; 40642-41-9P; 52957-10-5P; 56683-54-6P; 57393-02-9P; 68760-63-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, by Wittig reaction with in situ-generated phosphorane); 19101-00-9; 34626-52-3; 64417-10-3; 65734-62-5; 68760-65-6; 73945-70-7; 76771-95-4; 87436-78-0 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with sodium amide, in situ formation of ylide by); 23739-64-2; 50816-19-8 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with triphenylphosphine); 7782-92-5D; 7782-92-5D Role: RCT (Reactant), RACT (Reactant or reagent) (ylide premix of, with hydroxyalkyltriphenylphosphonium bromides)

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSCO  
Available on Infoscience
March 3, 2006
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/226828
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