TY - JOUR
T1 - The Unexpected Formation of 9,9,10,10-Tetrafluoro-1,2,4,12-tetraphenyl[2.2]paracyclophan-1-ene
AU - Roche, Alex J.
AU - Abboud, Khalil A.
AU - Dolbier, William R.
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/5/15
Y1 - 2015/5/15
N2 - An investigation of the palladium-catalyzed Kumada cross-coupling reaction between PhMgBr and (pseudo-ortho) 4,12-diiodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane revealed that in addition to the expected cross-coupled product, an unintended major product was generated. The product was determined to be 9,9,10,10-tetrafluoro-1,2,4,12-tetraphenyl[2.2]paracyclophan-1-ene by X-ray crystallography and is proposed to be formed via the first reported example of reductive defluorination by a Grignard reagent. (Chemical Equation Presented).
AB - An investigation of the palladium-catalyzed Kumada cross-coupling reaction between PhMgBr and (pseudo-ortho) 4,12-diiodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane revealed that in addition to the expected cross-coupled product, an unintended major product was generated. The product was determined to be 9,9,10,10-tetrafluoro-1,2,4,12-tetraphenyl[2.2]paracyclophan-1-ene by X-ray crystallography and is proposed to be formed via the first reported example of reductive defluorination by a Grignard reagent. (Chemical Equation Presented).
UR - http://www.scopus.com/inward/record.url?scp=84929598224&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84929598224&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.5b00657
DO - 10.1021/acs.joc.5b00657
M3 - Article
AN - SCOPUS:84929598224
SN - 0022-3263
VL - 80
SP - 5355
EP - 5358
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 10
ER -