Polychlorinated ketones. III. Formation by acid-catalyzed cleavage of vinyl phosphates and phosphonates

Novel phosphate anthelmintics. 3. Alkyl and aryl 1-methyleneallyl phosphates, phosphonates, and phosphinates

“…It appears that interaction between bulky substituents in the 1,1,3 positions of 1,3-butadiene (1,1,3 type of interaction) is necessary for twisting the molecule out of the strans conformation. 25 For hexachloro-1,3-butadiene there is strong evidence (ir, Raman) for a cisoid structure.24 '26 The unlikelihood of a completely s-cis structure due to halogen-halogen overlap supports this view.27 Hexachloro-1.3-butadiene and the pentachlorobutadienyl esters [13][14][15][16][17][18][19][20][21][22][23][24] have in effect two 1,1,3 interactions, strongly suggesting that they too exist in a cisoid conformation as indicated. Compounds 25-39 were readily synthesized by reaction of the appropriate trialkyl phosphite, dialkyl phosphonite, or methyl diphenylphosphinite with l,l,l,4,4-pentachloro-3buten-2-one (3) in ether.…”

Novel phosphate anthelmintics. 1. Alkyl 2,2-dichlorovinyl methyl phosphates and related alkoxyalkyl and cycloalkyl analogs of dichlorvos

“…Incomplete removal of 41 before distillation of 4 caused gradual and complete decomposition of this ester under distilling conditions to give pure dichloroacetaldehydet and an unidentified gas which may be isopropylene and methane as reported for similar cleavage of other vinyl phosphates. 27 The preparation of II by alcoholysis of the phosphochloridate III has been recently disclosed in the patent literature, Scheme III. ;poch=cci, VII aqueous me thy [cellulose.…”