Aliphatic semidiones. XXX. Alkenyl and cycloalkyl substituted 1,2-semidiones

Russell, Glen A.; Ballenegger, M.; Malkus, Herbert

doi:10.1021/ja00840a049

Cited by 11 publications

(3 citation statements)

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“…Prior to our work there was only one report about the preparation of an acetylenic 1,2‐dione, namely that of dodeca‐4,8‐diyne‐6,7‐dione, from pentynyllithium and oxalyl chloride 32. In our hands, this procedure was difficult to reproduce, giving rise to varying amounts of unstable product and, more importantly, was not generally applicable to other monosubstituted acetylenes.…”

Section: Resultsmentioning

confidence: 98%

The Modular Approach to Acetylenic Phthalocyanines and Phthalocyanine Analogues

Faust

2001

Eur. J. Org. Chem.

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The need for new chromophores with intense absorptions at the far red end or the near infrared region of the electromagnetic spectrum is evident from recent developments in materials science and medicinal chemistry. This has prompted us to explore the potential of octaalkynyl-substituted phthalocyanines, tetrapyrazinoporphyrazines, and tetra-6,7-quinoxalinoporphyrazines. In order to assemble these chromophores efficiently and in a modular fashion, we have prepared two types of acetylenic building blocks − namely 3,4-dimethylenehexa-1,5-diynes and hexa-1,5-diyne-3,4-diones − and have successfully converted them into alkynyl-substituted benzenoid phthalonitriles, the former by means of cycloaddi-

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Section: Resultsmentioning

confidence: 98%

The Modular Approach to Acetylenic Phthalocyanines and Phthalocyanine Analogues

Faust

2001

Eur. J. Org. Chem.

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“…[32] Accordingly, the detection of DMSO · and its decay has not been addressed in previous studies. [29][30][31][32] The reaction mechanism for electron transfer from DMF -to unsaturated compounds is probably not less ambiguous. [20] Whatever reservations can be forwarded on the electron-transfer mechanism from DMSO -and DMF -, Car (1) undeniably takes up electrons and is reduced to give the blue dianion Car 2-(3) (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…The presented method of generating dienolate anions by electron transfer to α,ω-polyene aldeydes refers to related prior research on generating anion radicals by single electron transfer to (un)-saturated mono or vicinal diketones. [29][30][31][32] Several oxocarotenoids have been exploratorily tested in alkaline DMSO and DMF. In this paper we concentrate to exemplify the reaction with 1 (Scheme 1).…”

Section: ·-mentioning

confidence: 99%