Neighboring group participation in the acetolysis of 1,1,1-triaryl-3-diazo-2-propanones. An unprecedented 1,3 shift of an aryl group via a five-membered transition state.
作者:Vittorio Rosnati、M.Luisa Di Vona、Alba Pusino、Antonio Saba
DOI:10.1016/s0040-4039(00)80453-0
日期:1988.1
The acetolysis of diazo ketones 1a,b,c, leads to the corresponding indanones 3a,b,c, and to the rearranged acetates 4a,b,c. The formation of the acetates 4 can be explained in terms of a mechanism involving the same transition state responsible for the ring closure to 3.
重氮酮1a,b,c的乙酰化反应产生相应的茚满酮3a,b,c和重排的乙酸酯4a,b,c。乙酸酯4的形成可以用涉及导致3环闭环的相同过渡态的机理来解释。