Cyclization and Aryne Chemistry

Arynes participate in three-component coupling reactions with N, S, P, and Se functionalities to yield 1,2-heteroatom-difunctionalized arenes. Using 2-iodophenyl arylsulfonates as benzyne precursors, we could effectively add magnesiated S-, Se-, and N-nucleophilic components to the strained triple bond. In the same po…

• MELİHA ÇETİN KORUKÇU

Dihydrobenzisoxazoles are readily prepared in good yields by the [3 + 2] cycloaddition of oxaziridines and arynes. The reaction involves an unusual cleavage of the C-O bond of the oxaziridine and tolerates a variety of substituents on the oxaziridine and the o-(trimethylsilyl)aryl triflate to form aryl-, heteroaryl-,…

• ARİF KIVRAK

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• SENEM AKKOÇ

Benzynes generated under Knochel conditions from 2-iodophenylsulfonates and (i)PrMgCl smoothly add to thiol, selenol, and amine nucleophiles. Treatment of the resulting aryl Grignard intermediate with a copper salt and an organic oxidant then affords symmetrical biaryls in good yield. 3-Substituted arynes undergo regi…

• MELİHA ÇETİN KORUKÇU

6pi electrocyclizations of dienylketenes to 2,4-cyclohexadienones have been investigated at the (U)B3LYP/6-31G level and found to be a favored and exothermic process for most dienylketenes. As evidenced by calculations, dienylketene cyclizations proceed via a pseudopericyclic process. If the terminal double bond of di…

• METİN ZORA

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of a New System Containing a Pyramidalized Double Bond: cis-Dicarbomethoxydihydroheptalene and Its Reaction with BenzyneAbdullah Menzek, Nurullah Saracoglu, Mariusz Krawiec, William H. Watson, and Metin BalciCite this: J. Org. Chem. 1995, 60, 4, 829–832Publication…

• NURULLAH SARAÇOĞLU

The [2 + 2] cycloadditions of cyclopentyne and benzyne to ethylene are explored at the B3LYP and CASSCF levels, supplemented by CCSD(T) and CAS-MP2 calculations at the stationary points. The biradical path in the benzyne system is computed to be about 4.1 kcal/mol lower than the concerted path, consistent with the exp…

• ARMAĞAN KINAL

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• ŞARON ÇATAK

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• AKIN SAĞIRLI

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• HALİL ŞENOL

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• ÇETİN BAYRAK
• ERTAN ŞAHİN

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTA seven-membered-ring allene dimer: synthesis of 1,2-benzo-1,3,4-cycloheptatriene and attempted synthesis of 1,2-benzo-1,4,5-cycloheptatrieneY. Kemal Yildiz, Hasan Secen, Mariusz Krawiec, William H. Watson, and Metin BalciCite this: J. Org. Chem. 1993, 58, 20, 5355–5359Publi…

• HASAN SEÇEN