0,Y-ethylenecarboxylic acid

A soln. of p-nitrobenzyl benzyloxycarbonyl-L-phenylalanyl-Nim.piperidinocarbo-nyl-L-histidylglycinate in abs. ethanol-dimethylacetamide allowed to react 15 hrs. at room temp, with 5 moles 100%-hydrazine hydrate -> benzyloxycarbonyl-L-phenylalanyl-L-histidylglycine hydrazide. Y 95%. F. e., also removal with NaOH, s. G. Jager, R. Geiger, and W. Siedel, B. 101, 3537 (1968) a,y -ethylenecarboxylic acid hydrazides from active esters s. R. Harada and H. Kondo, Bull. Chem. Soc. Japan 41, 2521 (1968). 

Ketones from a,y -ethylenecarboxylic acid esters Schmidt reaction... 

Cyclic p,Y-ethylenecarboxylic acids from p-spiro-p-lactones Cyclobex-l-enylacetic acids... 

N-Bromosuccinimide I sodium hydride I dimethy Iformamide 4-a-Bromo-2-azetidinones from p,y-ethylenecarboxylic acid amides... 

Fallacious acetatej 1,3-bis(diphenylphosphino)propane (E)-p,y-Ethylenecarboxylic acid amides from 2-ethyleneamines Carbonylation... 

E)-P,y-ethylenecarboxylic acid esters from acoxy-2-ethylenes 44, 722... 

Methylene-2-azetidinones from p-bromo-p,Y-ethylenecarboxylic acid amides Modified Ullmann-Goldberg reaction... 

A soln. of startg. a-chloroketimine in THF added to a soln of /-Pr2NLi in the same solvent at 0°, after 2 h acetone added dropwise, and stirring continued for 10 h with warming to room temp. - product. Y 80%. This is part of a 2-step synthesis of a,P-oxidoketones which cannot be obtained directly by the Darzens-Claisen route with diaryl ketones, P,y-ethylenecarboxylic acid amides were obtained with excess i-PrjNLi, especially in the presence of HMPA. F.e.s. P. Sulmon et al., J. Org. Chem. 53, 4457-62 (1988). 

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