synthesis and physicochemical investigation of
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Synthesis and Physicochemical Investigation of Hydrofluorocarbons with Extended p -Stacked Arene Units. Markus Etzkorn, Department of Chemistry, UNC Charlotte, 9201 University City Blvd., Charlotte, NC 28223. - PowerPoint PPT PresentationTRANSCRIPT
Synthesis and Physicochemical Investigation of
Hydrofluorocarbons with Extended -Stacked Arene Units
Markus Etzkorn, Department of Chemistry, UNC Charlotte, 9201 University City Blvd., Charlotte, NC 28223
Dienedione 3 is in principle an ideal framework to obtain scaffolds of type 6 by benzannulation and subsequent“coupling” of these intermediates. Since 3 is thermally labile the alcohol intermediates 7 and 8 are potential
Whereas diol 8 is prone to trans-annular reactions, hydroxyketone 7 provided a suitable Diels-Alder adduct 10 for functionalization: Dess-Martin oxidation yielded the formal DA-adduct 12 of the parent (3) which is thermally stable. Cycloaddition with TCTD (9) furnished the bis-adduct 14. Both DA adducts were converted with DDQ under mild conditions to their corresponding chlorinated arene derivatives 13 and 15.
O
O
O
OO
ORn
Rn
Rn
Rn
Rn
Rn
(R = H, F)3 4 6
(8)O (7)
OH
OH
OHNaBH4
O
O (3)
LiAlH4
O
7
OH SO2
Cl4
9 (TCTD)O
OH
ClCl
ClCl
10
O
ClCl
ClCl
O
Dess- Martinreagent
CH2Cl2 RT
O
Cl
ClCl
ClO
O
ClCl
ClCl
O
ClCl
Cl
Cl
OCl
ClCl
Cl
OCl
Cl
ClCl
toluene, rflx
13
14
15
DDQCH2Cl2
DDQCH2Cl2
9 (TCTD)
12
ORTEP plot of compound 12
intermediates towardtargets of type 6; wehave obtainedcrystal structures ofderivatives 3, 7 and 8.
Iso-Indenone Derivatives