51354-22-4

Upstream product

• 70654-44-3 (Z,E)-9,12-tetradecadien-1-ol 
• 108-24-7 acetic anhydride 
• 42521-46-0 Tetradeca-cis-9,trans-12-dien-1-ol 
• 29541-97-7 9-acetoxynonal 
• 98291-64-6 Triphenyl-((E)-1-trimethylsilanyl-pent-3-enyl)-phosphonium; bromide 
• 83488-96-4 (Z)-tetradeca-9,13-dien-1-yl acetate 
• 114157-22-1 9-(tert-butyl-dimethyl-silanyloxy)-1-nonanal 
• 157730-99-9 9-(tert-butyldimethylsilanyloxy)-1-nonanol 
• 3937-56-2 1,9-Nonanediol 
• 63591-90-2 1,3-propanediylidenebis(triphenylphosphorane) 
• 75-07-0 acetaldehyde 

Relevant academic research and scientific papers

Double-Bond Isomerization: Highly Reactive Nickel Catalyst Applied in the Synthesis of the Pheromone (9 Z,12 Z)-Tetradeca-9,12-dienyl Acetate

A highly reactive nickel catalyst comprising NiCl2(dppp) or NiCl2(dppe) with zinc powder, ZnI2 and Ph2PH, was applied in the isomerization of terminal alkenes to Z-2-alkenes. The double-bond geometry of the 2-alkene can be controlled via the reaction temperature to yield the 2-Z-alkenes in excellent yields and high Z-selectivities. The formation of other constitutional isomers, such as 3-alkenes, is suppressed on the basis of the proposed mechanism via a 1,2-hydride shift from the metal to the Ph2P ligand. The nickel-catalyzed isomerization reaction was then applied in the synthesis of (9Z,12Z)-tetradeca-9,12-dienyl acetate, a pheromone with a 2Z,5Z-diene subunit.

SYNTHESES WITH SULFONES XLVII : STEREOSELECTIVE ACCESS TO 1,3- AND 1,4-DIENES THROUGH HYDROGENOLYSIS OF BENZENESULFONYLDIENES. APPLICATION TO PHEROMONE SYNTHESIS.

The stereospecific reduction of EE 2-benzenesulfonyl-1,3-dienes to ZE 1,3-dienes with Grignard reagents under transition metal catalysis is described.Hydrogenolysis of the sulfonyl moiety of 2-benzenesulfonyl-1,4-dienes to ZE 1,4-dienes with sodium dithionite is reported.These techniques have been applied to the stereoselective synthesis of (7E, 9Z) dodecadienyl acetate 3d, (9Z, 11E) tetradecadienyl acetate 3e and (9Z, 12E) tetradecadienyl acetate, 6b.

Pheromones, XXXV. - Stereoselective Syntheses of 1,4-Alkadienes

The stereoselective synthesis of 1,4-alkadienes via Julia synthesis, Wittig reaction, Crombie synthesis and methylene interruption of conjugated alkadienylphosphonates is described.