Open Access1,1,3,3,3‐Pentafluoro‐2‐pentafluorophenylpropene oxide. Precursor for novel phosphonates and ylides
Author(s) -
Kadyrov Alexander A.,
Röschenthaler GerdVolker
Publication year - 1997
Publication title -
heteroatom chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.283
H-Index - 42
eISSN - 1098-1071
pISSN - 1042-7163
DOI - 10.1002/(sici)1098-1071(1997)8:1<59::aid-hc9>3.0.co;2-y
Subject(s) - phosphonate , chemistry , ylide , trimethylsilyl , oxide , epoxide , medicinal chemistry , hydrolysis , organic chemistry , catalysis
1,1,3,3,3‐Pentafluoro‐2‐pentafluorophenylpropene oxide reacted with triethyl phosphite to give the ylide C 6 F 5 (CF 3 )C=P(OEt) 3 . Hydrolysis yielded the phosphonate C 6 F 5 (CF 3 )CHP(O)(OEt) 2 , which was dehydrofluorinated using Et 3 N · BF 3 to form the vinyl phosphonate C 6 F 5 (CF 2 =)CP(O)(OEt) 2 , a compound available also directly from the starting epoxide and diethyl trimethylsilyl phosphite. The vinyl phosphonate and diethyl trimethylsilyl phosphite furnished a 2:1 mixture of (Z) and (E) bisphosphonates together with fluorotrimethylsilane. Thermolylsis of the ylide gave diethyl phosphorofluoridate and 1,1‐difluoro‐2‐pentafluorophenyl‐but‐1‐ene. © 1997 John Wiley & Sons, Inc.