




Under acid conditions of hydrolysis, methanol, acetone, ortho- 
phosphoric acid, methyl phosphoric acid, and N,N-(CH3),-acetoacetamide 
were all identified. Some dimethylamine was probably also present. 
Thus, acid hydrolysis proceeded by initial loss of a methoxy-group 
followed by rapid loss of the crotonamide. Some chromatograms suggested 
the formation of desmethoxy bidrin or azodrin, both high unstable in acid 
solution. Even after 6 hours of refluxing, significant quantities of 
dimethylacetoacetamide were present. The stability of the amide group 
in bidrin indicated that 3-(dimethoxyphosphinyloxy)crotonic acid and its 
des-methoxy derivatives were not part of the major decomposition path (193). 
Q CH3 ¢) R 
(CH,.0) ,-P-0-C=CH-C_N” 
Sf 2 N 
CH, 
+ cers 
H , H,0 (rate determining step) 
Q a # 
cag frantic ta © + MeOH 
Gu cH, ‘cH, 
H+, H,0 (rapid) 
hs Nae aN ten Sou Ry 
3) gaa Hers 
OH cH, 
H0 
0 0 R 
HO-P 4- + MeOH + CH,-C-CH. + C , a 
_— Po e =-_( = ay 
: ; 0, + (NH,-CH,) 
OH 
R= Methyl (Bidrin) 
or= H (azodrin) 
59 
