Anodic coupling of carboxylic acids to electron-rich double bonds: A surprising non-Kolbe pathway to lactones

• Robert J. Perkins,
• Hai-Chao Xu,
• John M. Campbell and
• Kevin D. Moeller

Beilstein J. Org. Chem. 2013, 9, 1630–1636, doi:10.3762/bjoc.9.186

• appear to proceed through an olefinic radical cation intermediate. Results and Discussion Initial cyclization studies The compatibility of the carboxylic acid with the anodic cyclization was initially studied by examining the anodic oxidation of substrates 14a–c (Table 1). The oxidation of 14a nicely

• readily as radical 21a. Indeed, the anodic oxidation of 19g gave low yields and poor current efficiency, mirroring the results obtained from the oxidation of unsubstituted styrene 19a. As with other substrates, the oxidation potential of 19g was lower than that of its seven-membered ring counterpart 19h

Efficient electroorganic synthesis of 2,3,6,7,10,11-hexahydroxytriphenylene derivatives

• Carolin Regenbrecht and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2012, 8, 1721–1724, doi:10.3762/bjoc.8.196

• [11][12]. Furthermore, no transition metal cations, which promote the cleavage of the ketal moiety [11], are involved. The anodic oxidation of catechol derivatives was first demonstrated by Parker et al. [13]. Applying this methodology in a specific electrolysis cell, Simonet et al. established a

• Anodic oxidation of catechol ketals We report a simple protocol for the anodic oxidation of catechol ketals forming triphenylene ketals (Scheme 1). Best results were obtained in PC and TMABF4 (method A) or TBABF4 (method B) as electrolytes. Performing the reaction in PC is beneficial for several reasons

• . However, our method provides easy access to pure 3 which can easily be separated and purified by simple filtration. Conclusion Triphenylene ketals are easily available by anodic oxidation using a simple galvanostatic protocol. Best results are obtained when the synthesized dehydrotrimers are almost

Conjugated polymers containing diketopyrrolopyrrole units in the main chain

• Bernd Tieke,
• A. Raman Rabindranath,
• Kai Zhang and
• Yu Zhu

Beilstein J. Org. Chem. 2010, 6, 830–845, doi:10.3762/bjoc.6.92

• easily electropolymerized by anodic oxidation. An insoluble, non-luminescent polymer film formed at the electrode that exhibited reversible electrochromic properties (Table 4). The film could be switched from blue in the neutral state via transparent grey to purple red in the oxidized state. The

Generation of pyridyl coordinated organosilicon cation pool by oxidative Si-Si bond dissociation

• Toshiki Nokami,
• Ryoji Soma,
• Yoshimasa Yamamoto,
• Toshiyuki Kamei,
• Kenichiro Itami and
• Jun-ichi Yoshida

Beilstein J. Org. Chem. 2007, 3, No. 7, doi:10.1186/1860-5397-3-7

• ]. The coordination also stabilizes the thus-generated radical cation and weakens the C-Sn bond. A similar effect of intramolecular coordination was observed in the case of silicon [23]. Another important point is that pyridyl group is rather inactive toward the anodic oxidation. Thus, we chose to use a