e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Carbene reactions with cis azo functions. Formation of ester azines from. DELTA. 3-1, 3, 4-oxadiazolines

D Keus, M Kaminski, J Warkentin

Index: Keus, Diane; Kaminski, Maciej; Warkentin, John Journal of Organic Chemistry, 1984 , vol. 49, # 2 p. 343 - 347

Full Text: HTML

Citation Number: 26

Abstract

Thermolysis of a 2-alkoxy-2, 5, 5-trialkyl-A3-1, 3, 4-oxadiazoline (l), either neat or in a solvent such as benzene, leads to a carbonyl ylide intermediate which fragments to carbonyl compounds and carbenes. The latter attack the parent oxadiazoline at the azo function, presumably to form azomethine imine ylides. The latter ylides then fragment to form carbonyl compounds and azines such as R1 (R20) C= NN= C (OR2) R1, R1 (R20) C= NN= C (R3) ...

Ethanol Structure

Acetic acid,2-(1-methylethylidene)hydrazide Structure

Acetic acid,2-(...

~%

2-ethoxy-2,5,5-trimethyl-1,3,4-oxadiazole Structure

2-ethoxy-2,5,5-...

2-acetoxy-2,5,5-trimethyl-2,5-dihydro-[1,2,4]oxadiazole Structure

2-acetoxy-2,5,5...

2,2,5-trimethyl-5-(2,2,2-trifluoroethoxy)-1,3,4-oxadiazole Structure

2,2,5-trimethyl...

~%

2,2,2-Trifluoroethyl Acetate Structure

2,2,2-Trifluoro...

2,2,2-trifluoroethylN-(propan-2-ylidene)acetohydrazonate Structure

2,2,2-trifluoro...

acetone azine Structure

2,2,5-trimethyl-5-(2,2,2-trifluoroethoxy)-1,3,4-oxadiazole Structure

2,2,5-trimethyl...

~%

2,2,2-Trifluoroethyl Acetate Structure

2,2,2-Trifluoro...

2,2,2-trifluoroethylN-(propan-2-ylidene)acetohydrazonate Structure

2,2,2-trifluoro...

Acetone Structure

Ethapon Structure

Acetic acid,2-(1-methylethylidene)hydrazide Structure

Acetic acid,2-(...

~%

2,2,5-trimethyl-5-(2,2,2-trichloroethoxy)-1,3,4-oxadiazole Structure

2,2,5-trimethyl...

2-acetoxy-2,5,5-trimethyl-2,5-dihydro-[1,2,4]oxadiazole Structure

2-acetoxy-2,5,5...

2,2,2-Trifluoroethanol Structure

2,2,2-Trifluoro...

Acetic acid,2-(1-methylethylidene)hydrazide Structure

Acetic acid,2-(...

~%

2,2,5-trimethyl-5-(2,2,2-trifluoroethoxy)-1,3,4-oxadiazole Structure

2,2,5-trimethyl...

2-acetoxy-2,5,5-trimethyl-2,5-dihydro-[1,2,4]oxadiazole Structure

2-acetoxy-2,5,5...

2,2,5-trimethyl-5-(2,2,2-trichloroethoxy)-1,3,4-oxadiazole Structure

2,2,5-trimethyl...

~%

2,2,2-trichloroethyl acetate Structure

2,2,2-trichloro...

2,2,2-trichloroethylN-(propan-2-ylidene)acetohydrazonate Structure

2,2,2-trichloro...

acetone azine Structure

2,2,5-trimethyl-5-(2,2,2-trichloroethoxy)-1,3,4-oxadiazole Structure

2,2,5-trimethyl...

~%

2,2,2-trichloroethyl acetate Structure

2,2,2-trichloro...

2,2,2-trichloroethylN-(propan-2-ylidene)acetohydrazonate Structure

2,2,2-trichloro...

Acetone Structure

Acetic acid,2-(1-methylethylidene)hydrazide Structure

Acetic acid,2-(...

~%

ethyl N-propan-2-ylideneethanehydrazonate Structure

ethyl N-propan-...

2-ethoxy-2,5,5-trimethyl-1,3,4-oxadiazole Structure

2-ethoxy-2,5,5-...

~%

2-(1-ethoxyethoxy)prop-1-ene Structure

2-(1-ethoxyetho...

ethyl N-propan-2-ylideneethanehydrazonate Structure

ethyl N-propan-...

ethyl acetate Structure

Detail

2-ethoxy-2,5,5-trimethyl-1,3,4-oxadiazole Structure

2-ethoxy-2,5,5-...

~%

propene Structure

ethyl N-propan-2-ylideneethanehydrazonate Structure

ethyl N-propan-...

acetone azine Structure

2-ethoxy-2,5,5-trimethyl-1,3,4-oxadiazole Structure

2-ethoxy-2,5,5-...

~%

propene Structure

2-(1-ethoxyethoxy)prop-1-ene Structure

2-(1-ethoxyetho...

ethyl N-propan-2-ylideneethanehydrazonate Structure

ethyl N-propan-...

Detail

2-ethyl-2-methoxy-5,5-dimethyl-2,5-dihydro-1,3,4-oxadiazole Structure

2-ethyl-2-metho...

~%

propene Structure

methyl N-propan-2-ylidenepropanehydrazonate Structure

methyl N-propan...

acetone azine Structure

2-ethoxy-2,5,5-trimethyl-1,3,4-oxadiazole Structure

2-ethoxy-2,5,5-...

~%

propene Structure

ethyl N-propan-2-ylideneethanehydrazonate Structure

ethyl N-propan-...

acetone azine Structure

2,2,5-trimethyl-5-(2,2,2-trichloroethoxy)-1,3,4-oxadiazole Structure

2,2,5-trimethyl...

~%

2,2,2-trichloroethyl acetate Structure

2,2,2-trichloro...

2,2,2-trichloroethylN-(propan-2-ylidene)acetohydrazonate Structure

2,2,2-trichloro...

acetone azine Structure

2,2,5-trimethyl-5-(2,2,2-trifluoroethoxy)-1,3,4-oxadiazole Structure

2,2,5-trimethyl...

~%

2,2,2-Trifluoroethyl Acetate Structure

2,2,2-Trifluoro...

2,2,2-trifluoroethylN-(propan-2-ylidene)acetohydrazonate Structure

2,2,2-trifluoro...

acetone azine Structure

2-ethoxy-5,5-dimethyl-2-propan-2-yl-1,3,4-oxadiazole Structure

2-ethoxy-5,5-di...

~%

ethyl (E)-N-(propan-2-ylidene)isobutyrohydrazonate Structure

ethyl (E)-N-(pr...

Ethyl isobutyrate Structure

Ethyl isobutyrate

acetone azine Structure

2-ethoxy-2,5,5-trimethyl-1,3,4-oxadiazole Structure

2-ethoxy-2,5,5-...

~%

propene Structure

2-(1-ethoxyethoxy)prop-1-ene Structure

2-(1-ethoxyetho...

ethyl N-propan-2-ylideneethanehydrazonate Structure

ethyl N-propan-...

Detail

N-(propan-2-ylideneamino)propanamide Structure

N-(propan-2-yli...

~%

methyl N-propan-2-ylidenepropanehydrazonate Structure

methyl N-propan...

2-ethyl-2-methoxy-5,5-dimethyl-2,5-dihydro-1,3,4-oxadiazole Structure

2-ethyl-2-metho...

~%

propene Structure

methyl N-propan-2-ylidenepropanehydrazonate Structure

methyl N-propan...

acetone azine Structure

1-(4-hydroxybutanoyl)-2-(1-methylethylidene)hydrazine Structure

1-(4-hydroxybut...

~61%

2,2-dimethyl-1,6-dioxa-3,4-diazaspiro[4.4]non-3-ene Structure

2,2-dimethyl-1,...

Acetic acid,2-(1-methylethylidene)hydrazide Structure

Acetic acid,2-(...

~%

2-(1-ethoxyethoxy)prop-1-ene Structure

2-(1-ethoxyetho...

2-ethoxy-2,5,5-trimethyl-1,3,4-oxadiazole Structure

2-ethoxy-2,5,5-...

~%

2-(1-ethoxyethoxy)prop-1-ene Structure

2-(1-ethoxyetho...

ethyl N-propan-2-ylideneethanehydrazonate Structure

ethyl N-propan-...

ethyl acetate Structure

Detail

2-ethoxy-2,5,5-trimethyl-1,3,4-oxadiazole Structure

2-ethoxy-2,5,5-...

~%

propene Structure

2-(1-ethoxyethoxy)prop-1-ene Structure

2-(1-ethoxyetho...

ethyl N-propan-2-ylideneethanehydrazonate Structure

ethyl N-propan-...

Detail