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Versuche zur Synthese von α,β‐ungesättigten trifluormethylierten Aldehyden
Author(s) -
Abele Herbert,
Haas Alois,
Lieb Max
Publication year - 1986
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19861191127
Subject(s) - chemistry , hexafluoroacetone , yield (engineering) , hydrolysis , trifluoromethyl , medicinal chemistry , bromide , bromine , stereochemistry , organic chemistry , materials science , alkyl , metallurgy
Efforts in Synthesizing α,β‐Unsaturated Trifluoromethyl‐substituted Aldehydes Hexafluoroacetone reacts with ethynylmagnesium bromide to yield (CF 3 ) 2 C(OH) C CH ( 1 ). Bromine can be added to the triple bond affording the cis/trans ‐isomer 2 . With PCl 5 1 yields the allene (CF 3 ) 2 CCCClH ( 3 ). The addition of a metalated Schiff base to hexafluoroacetone leads to 4a which on hydrolysis yields (CF 3 ) 2 C(OH) CH 2 CHO ( 4b ). The reaction of (EtO) 2 P(O)CH 2 R (RCHO, CO 2 Et) with hexafluoroacetone gives α,β‐unsaturated aldehydes or esters 6 . 1,1,1‐Trifluoroacetone provides analogous reactions.