86299-98-1

Upstream product

• 34859-61-5 ethyl 2-amino-5,5-dimethyl-4,5-dihydro-3-furancarboxylate 
• 2526-64-9 dichlorotriphenylphosphorane 

Downstream Products

• 103148-80-7 6,7-Dicyan-2,3,3a,7a-tetrahydro-2,2-dimethyl-4-(triphenylphosphoranylidenamino)benzofuran-3a-carbonsaeure-ethylester 
• 86300-10-9 3-Ethyl-5,5-dimethyl-2-(triphenylphosphonioimino)-tetrahydro-3-furancarbonsaeure-ethylester-iodid 
• 86300-22-3 6,7-Dihydro-7,7-dimethyl-2-(triphenylphosphoranylidenamino)-3,5-oxepindicarbonsaeure-5-ethylester-3-methylester 
• 86300-26-7 6,7-Dihydro-7,7-dimethyl-2-(triphenylphosphoranylidenamino)-3,4,5-oxepintricarbonsaeure-5-ethylester-3,4-dimethylester 
• 86300-07-4 3,5,5-Trimethyl-2-(triphenylphosphonioimino)-tetrahydro-3-furancarbonsaeure-ethylester-iodid 

Relevant academic research and scientific papers

Heterocyclic β-Enamino Esters, 30. Synthesis and Cycloaddition-Ring Expansion Sequence of Iminophosphoranes of Heterocyclic β-Enamino Esters: 6,7-Dihydrooxepins, thiepins, and 3,4-Dihydro-2H-thiocins

The heterocyclic β-enamino esters 1a - d, 2a - c, 5, and 6 react in the system triphenylphosphane/hexachloroethane/triethylamine in high yields to afford the resonance-stabilized iminophosphoranes 3a - d, 4a - c, 7, and 8.Alkyl iodides attack the electron rich C-β in 3a - d; the phosphonium salts 11a - h thus obtained split with alkaline into the imines 12a - h.With acetylenecarboxylic esters in a cycloaddition-ring expansion sequence from 3a - d, 4a - c, 7, and 8 dihydrooxepins 14a - h, 15a - c, e - g, dihydrothiepins 16a, b, and dihydro-2H-thiocins 17a, b, respectively, are formed in high yields.Acid-catalyzed hydrolysis of 14c, d leads to the enamino esters 19a, b.