A new development in the chemistry of arenes activated toward S(N)Ar reactions by the cyclopentadienyliron (FeCp+) moiety is presented in this work. A class of diiron complexes of diphenoxybenzenes was prepared in a highly efficient and very mild fashion. Dihydroxyaromatic compounds served as dinucleophiles, allowing for the formation of the diiron complexes. This could be achieved in either a one or two step procedure. A wide variety of dinucleophiles were incorporated into this study, as well as a number of FeCp+ activated arenes. It is shown that these reactions are not inhibited by bulky substituents on either the dinucleophiles or activated arenes. The diiron complexes themselves could also undergo S(N)Ar reactions, provided that the complexed arenes contained a chlorine substituent. This allowed for the functionalization of the complexes with species that could not be introduced directly in their syntheses. The carbon nucleophiles generated from ethyl cyanoacetate or (phenylsulfonyl)acetonitrile could be attached to the complexed ethers in this manner. The FeCp+ moieties were removed easily by photolytic demetalation which allowed for the recovery of a wide range of functionalized diphenoxybenzenes. This methodology is advantageous over all those previously reported and should be a practical route to the synthesis of aromatic ethers.
A phtalide compound and a near infrared absorber and a recording material each comprising the same compound
申请人:YAMAMOTO CHEMICALS, INC.
公开号:EP0664292A1
公开(公告)日:1995-07-26
A phthalide compound of general formula (I) and a near infrared absorber and a recording material each utilizing the phthalide compound are disclosed.
wherein ring A represents a substituent group of the following formula
where R₁ represents hydrogen, alkyl, alkoxy or halogen; n represents an integer of 1-3; ring B represents a defined aromatic ring; R₂ represents alkyl or aryl; R₃ represents alkyl; R₄ and R₅ independently represent alkyl or unsubstituted or substituted phenyl; R₆ represents hydrogen, alkyl or alkoxy.
The near infrared absorber and the recorded image on the recording material absorb strongly the near infrared region with no appreciable absorption in the visible region of the spectrum. The near infrared absorber is colorless or pale in color and yet highly capable of absorbing near infrared radiation. The recorded image on the recording material can hardly be read with the eye but can be read with the OCR. Moreover, the effect on the developed shade of any concomitant color former in a recording material is minimal.
Selective displacement of aryl fluorides with hydroquinone: synthesis of 4-phenoxyphenols
作者:Benjamin F. Marcune、Michael C. Hillier、Jean-François Marcoux、Guy R. Humphrey
DOI:10.1016/j.tetlet.2005.09.025
日期:2005.11
The selective displacement of a variety of aryl fluorides with hydroquinone has been achieved to give substituted 4-phenoxyphenols 3. In some cases the addition of 18-crown-6 resulted in a significant rate enhancement, and the reactions could be carried out at lower temperature. One of these derivatives, 3a (X = Cl) was converted to 2-propyl-4-(4-chlorophenoxy)phenol 2a, a precursor to the PPAR gamma receptor agonist 1. (c) 2005 Elsevier Ltd. All rights reserved.
Salicylic acid derivatives, the process for preparing the same and the heat-sensitive recording materials comprising thereof