
%0 Journal Article
%A Black, DSC 
%A Eastwood, FW 
%A Okraglik, R 
%A Poynton, AJ 
%T Claisen rearrangement of allyl imidates and thioimidates derived from lactams and thiolactams
%J Australian Journal of Chemistry
%D 1972/07/01
%V 25
%N 7
%P 1483-1494
%K 
%R https://doi.org/10.1071/CH9721483
%U https://www.publish.csiro.au/paper/CH9721483 
%X Allyl imidates N=C(OCH2CH=CH2)CH2, derived from lactams, rearrange on heating to yield the corresponding C-allyl and N-dlyl lactams,I     NHCOCHCH2CH=CH2 and N(CH2CH=CH2)COCH2  while allyl thioimidates yield only the C-allyl thiolactams. The C-allylation is postulated to occur through a ketene acetal intermediate by way of a quasi-chair transition state. The yield of 3-allylhexahydro-2H-azepin-2-one obtained in such a rearrangement is significantly increased by the presence of 2-pyridone. 
