16116-86-2Relevant articles and documents
Production of [pisen[pisen] and derivatives thereof
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Paragraph 0036, (2017/07/07)
PROBLEM TO BE SOLVED: To provide a method of producing a picene and a derivative thereof suitable for uses of organic semiconductors, thin film transistors, field effect transistors or solar batteries or the like, in a short reaction process with high yield.SOLUTION: A method of producing a picene of formula 8 and a derivative thereof includes, as represented compounds and steps, a step 1 to subject a compound of formula 5 and a compound of formula 6 to a coupling reaction for producing a compound of formula 7, and a step 2 to subject the compound of formula 7 to dehydrohalogenation.
Dimetallation of phenylacetylene. Synthesis of ortho-susbtituted derivatives of phenylacetylene, benzoselenophene and benzotellurophene
Brandsma, L.,Hommes, H.,Verkruijsse, H. D.,Jong, R. L. P. de
, p. 226 - 230 (2007/10/02)
Phenylacetylene can be dimetallated in two ways. o-K-C6H4-CC-Li is formed by treating phenylacetylene at -70 deg C with two equivalents of butyllithium and one equivalent of potassium tert-butoxide in a mixture of tetrahydrofuran and hexane.The dimetallation with BuLi*N,N,N',N'-tetramethylethanediamine (TMEDA) affords a mixture of about 15percent (m + p)-Li-C6H4-CCLi and 85percent o-LiC6H4-CC-Li.Ortho-K-C6H4-CC-Li can be transformed into the dilithio or di-Grignard derivatives by addition of anhydrous lithium bromide or magnesium bromide etherate.Reaction of the dilithio derivative with elemental selenium and tellurium, followed by successive addition of tert-butyl alcohol and hexamethylphosphoric triamide (HMPT), gives benzoselenophene and benzotellurophene in good yields.Regiospecific functionalization of the nucleus via dimetal derivatives succeeds in the case of alkylation, halogenation, sulfenylation and acylation (with dimethylformamide and dimethylacetamide).Trimethylchlorosilane, chloromethyl methyl ether, aldehydes and ketones do not however react regiospecifically.
