(Bio)isosteres of ortho- and meta-substituted benzenes

• H. Erik Diepers and
• Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

Honeycomb reactor: a promising device for streamlining aerobic oxidation under continuous-flow conditions

• Masahiro Hosoya,
• Yusuke Saito and
• Yousuke Horiuchi

Beilstein J. Org. Chem. 2023, 19, 752–763, doi:10.3762/bjoc.19.55

• at room temperature (Table 1, entry 1). However, four kinds of catalysts were used, and a simpler catalytic system would be preferable. The highly reactive catalyst, 9-azanoradamantane N-oxyl (nor-AZADO), was tried with NaNO2 as a cocatalyst, which resulted in completion of the reaction in 60 min

• (Table 1, entry 2) [39]. While this led to a simpler catalyst system, nor-AZADO is expensive. Hong and co-workers have developed a low-cost catalyst system using TEMPO and nitrate salts [40]. Fe(NO3)3 (Table 1, entry 3), Cu(NO3)2 (Table 1, entry 4), Zn(NO3)2 (Table 1, entry 5) worked as catalysts

Metal-free mechanochemical oxidations in Ertalyte^® jars

• Andrea Porcheddu,
• Francesco Delogu,
• Lidia De Luca,
• Claudia Fattuoni and
• Evelina Colacino

Beilstein J. Org. Chem. 2019, 15, 1786–1794, doi:10.3762/bjoc.15.172

• l’Ecole Normale, 34296 Montpellier, Cedex 5, France 10.3762/bjoc.15.172 Abstract Aimed at eliminating or at least significantly reducing the use of solvents, sodium hypochlorite pentahydrate crystals (NaOCl·5H2O) in the presence of a catalytic amount of a nitrosyl radical (TEMPO or AZADO) have been

• a mechanochemical process. Keywords: AZADO; Ertalyte®; green chemistry; mechanochemistry; NaOCl·5H2O; selective oxidation; TEMPO; Introduction The conversion of primary and secondary alcohols to the corresponding carbonyl compounds (aldehydes and ketones, respectively) is of such importance in

• . In particular, in this study, we used sodium hypochlorite pentahydrate (NaOCl·5H2O) in the presence of a catalytic amount of a nitrosyl radical (TEMPO or AZADO) to induce mechanochemical oxidation reactions on suitably selected primary and secondary alcohols. Performed in a high-energy ball mill and

Structures of the reaction products of the AZADO radical with TCNQF₄ or thiourea

• Hideto Suzuki,
• Yuta Kawahara,
• Hiroki Akutsu,
• Jun-ichi Yamada and
• Shin’ichi Nakatsuji

Beilstein J. Org. Chem. 2013, 9, 1487–1491, doi:10.3762/bjoc.9.169

• reaction of AZADO (2-azaadamantane N-oxyl) with TCNQF4 (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane), the reaction of AZADO with thiourea provided an inclusion compound, in which AZADO molecules are incorporated in cylindrical channels formed by thiourea molecules. Keywords: adduct; inclusion

• including oxygen [1]. Sometimes, however, the merit turns out to be a drawback by limiting its properties and reactivity. For example, 1 is inefficient in the oxidation of sterically hindered secondary alcohols. The AZADO radical (2) [2] is an intriguing nitroxide radical with adamantane-like structure and

• impressively some TEMPO derivatives with appropriate acceptor units such as 1,4-benzoquinone [7] or naphthalenediimide [8] can form single-component CT complexes by self-assembly. Based on previous results, we next intended to see if similar CT complexes would be formed from AZADO (2) with an appropriate