62994-00-7

Upstream product

• 110-65-6 1,4-dihydroxybut-2-yne 
• 67-66-3 chloroform 
• 7553-56-2 iodine 
• 854470-08-9 2-chloro-3-hydroxy-1-hydroxymethyl-propenylmercury ⁽¹⁺⁾; chloride 

Downstream Products

• 110-65-6 1,4-dihydroxybut-2-yne 

Relevant academic research and scientific papers

BUT-2-ENE-1, 4-DIOLS AND METHODS FOR THE PREPARATION THEREOF

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

Syntheses of 7-Substituted Anthra[2,3- b]thiophene Derivatives and Naphtho[2,3- b:6,7- b']dithiophene

7-R-Anthra[2,3-b]thiophene derivatives (1, R = H, Me, i-Pr, or MeO) are prepared in three steps (in average overall yield >50%) starting from (E)-4-RC6H4CH2(HOCH2)C=CI(CH2OH). The latter are commercial or readily prepared from 2-butyne-1,4-diol and ArCH2Cl (both costing 1 cent/mmol) at 10 g scales. These allow for the selective formation of (otherwise unattainable) higher solubility 7-derivatives. Similar methods allow for the preparation of naphtho[2,3-b:6,7-b']dithiophene 2 using equally low-cost starting materials.

Straightforward Synthesis of 2- and 2,8-Substituted Tetracenes

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.

BORONIC ACID CATALYSTS AND METHODS OF USE THEREOF FOR ACTIVATION AND TRANSFORMATION OF CARBOXYLIC ACIDS

The present application provides methods and catalysts for activation of carboxylic acids for organic reactions. In particular, methods are disclosed for direct nucleophilic addition reactions, such as, amidation reactions with amines, cycloadditions, and conjugate additions, using boronic acid catalysts of formula I, II or III: Also included are novel boronic acid catalysts of formula IV, V and III:

Room-temperature carbonization of poly(diiododiacetylene) by reaction with Lewis bases

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.

X-ray contrast agents

This invention describes a new type of X-ray contrast agents. It has been found that iodinated alkenes containing one or several C═C double bonds substituted with electronic neutral substituents and iodine can be used as X-ray contrast agents. Also new iodoalkene compounds are described.

X-ray contrast agents

The invention describes a new type of X-ray contrast agent. It has been found that iodinated alkenes with one or more C=C double bonds substituted with electronically neutral substituents and iodine can be used as X-ray contrast agents. Novel iodoalkene compounds are also described.