67079-92-9Relevant academic research and scientific papers
THERMAL AND PHOTOCHEMICAL REACTIONS OF BIACETYL WITH 1,1-DIETHOXYETHENE. "UMPOLUNG" OF THE REACTIVITY OF BIACETYL BY PHOTOCHEMICAL INDUCED ELECTRON TRANSFER.
Mattay, Jochen,Gersdorf, Joachim,Freudenberg, Ulrich
, p. 817 - 820 (1984)
The thermal and photochemical reactions of biacetyl 1 and 1,1-diethoxyethene 2 are totally complementary: 1 and 2 exclusively form the 2,2-diethoxyoxetane 4 in polar solvents at room temperature.Contrary to the literature this thermal cycloaddition proceeds uncatalyzed. 1 and 2 react photochemically under exclusive formation of the regioisomer oxetane 3 - preferably in nonpolar solvents.The inversion ("Umpolung") of the reactivity of 1 is caused by the photoinduced electron transfer.
Additions of 1,1-Diethoxyethene to 1,2-Diketones
Mattay, Jochen,Runsink, Jan
, p. 2815 - 2818 (2007/10/02)
The ketene acetal 2 undergoes thermally noncatalyzed additions to various 1,2-diketones under formation of - and -adducts.Only with biacetyl 1a could an oxetane, 3, be isolated whereas mainly substituted 6-oxo-2,4-hexadienoic acid ethyl esters 6 and 7 are formed with aromatic 1,2-diketones.The regioselectivities and the product ratios are discussed in terms of a mechanism via zwitterionic intermediates.
