62994-00-7Relevant articles and documents
BUT-2-ENE-1, 4-DIOLS AND METHODS FOR THE PREPARATION THEREOF
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Page/Page column 13-14, (2018/04/17)
Compounds are provided that are useful synthetic intermediates, particularly for the preparation of dialdehydes. The compounds have the formula (I): wherein Z is I, Br or CH2Ar2; Ar1 is 4-Y1C6H4
Straightforward Synthesis of 2- and 2,8-Substituted Tetracenes
Woodward, Simon,Ackermann, Miriam,Ahirwar, Saurabh K.,Burroughs, Laurence,Garrett, Mary Robert,Ritchie, John,Shine, Jonathan,Tyril, Bj?rk,Simpson, Kevin,Woodward, Peter
supporting information, p. 7819 - 7824 (2017/06/06)
A simple regiospecific route to otherwise problematic substituted tetracenes is described. The diverse cores (E)-1,2-Ar1CH2(HOCH2)C=C(CH2OH)I (Ar1=Ph, 4-MePh, 4-MeOPh, 4-FPh) and (E)-1,2-I(HOCH2)C=C(CH2OH)I, accessed from ultra-low cost HOCH2C≡CCH2OH at multi-gram scales, allow the synthesis of diol libraries (E)-1,2-Ar1CH2(HOCH2)C=C(CH2OH)CH2Ar2 (Ar2=Ph, 4-MePh, 4-iPrPh, 4-MeOPh, 4-FPh, 4-BrPh, 4-biphenyl, 4-styryl; 14 examples) by efficient Negishi coupling. Copper-catalysed aerobic oxidation cleanly provides dialdehydes (E)-1,2-Ar1CH2(CHO)C=C(CHO)CH2Ar2, which in many cases undergo titanium(IV) chloride-induced double Bradsher closure, providing a convenient method for the synthesis of regiochemically and analytically pure tetracenes (12 examples). The sequence is typically chromatography-free, scalable, efficient and technically simple to carry out.
Room-temperature carbonization of poly(diiododiacetylene) by reaction with Lewis bases
Luo, Liang,Resch, Daniel,Wilhelm, Christopher,Young, Christopher N.,Halada, Gary P.,Gambino, Richard J.,Grey, Clare P.,Goroff, Nancy S.
supporting information; experimental part, p. 19274 - 19277 (2012/01/06)
Poly(diiododiacetylene) (PIDA) is a conjugated polymer containing an all-carbon backbone and only iodine atom substituents. Adding a Lewis base to the blue PIDA suspension at room temperature leads first to rapid disappearance of the absorption peaks attributed to PIDA, followed more slowly by release of free iodine. The resulting solid material gives a Raman scattering spectrum consistent with graphitic carbon, and it has a much higher conductivity than PIDA itself. Further investigation has led to the discovery of a previously unreported transformation, the reaction of a Lewis base such as pyrrolidine with a trans-diiodoalkene to form the corresponding alkyne. The generality of this iodine elimination further suggests that reaction of PIDA with Lewis bases dehalogenates the polymer, presenting a new method to prepare carbon nanomaterials at room temperature under very mild conditions.