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

(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)]


Published in:
Tetrahedron Letters, 26, 3, 307-10
Year:
1985
Keywords:
Note:
CAN 103:6067
26-2
Biomolecules and Their Synthetic Analogs
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0040-4039
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)
Laboratories:




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


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)