
TY  - JOUR
A1  - Black, DSC 
A1  - Eastwood, FW 
A1  - Okraglik, R 
A1  - Poynton, AJ 
T1  - Claisen rearrangement of allyl imidates and thioimidates derived from lactams and thiolactams
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1972
VL  - 25
IS  - 7
SP  - 1483
EP  - 1494
KW  - 
UR  - https://doi.org/10.1071/CH9721483 
N2  - 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. 
ER  -

