Atherton–Todd reaction: mechanism, scope and applications

• Stéphanie S. Le Corre,
• Mathieu Berchel,
• Hélène Couthon-Gourvès,
• Jean-Pierre Haelters and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2014, 10, 1166–1196, doi:10.3762/bjoc.10.117

• ), used as a base in the AT reaction) probably reacted first with carbontetrachloride to produce a charge-transfer complex (this type of interaction was confirmed by refractometric titration). However, in this reaction the trichloromethylphosphonate, which would result from the reaction of the anion CCl3

• − with chlorophosphate, was never observed because CCl3− probably reacted as a base in the presence of dialkylphosphite (Scheme 3-ii). This experiment indicates that the basicity/nucleophilicity of the amine has an impact on the first step of the mechanism (a charge-transfer complex was not observed with

Molecular assembly of amino acid interlinked, topologically symmetric, π-complementary donor–acceptor–donor triads

• M. B. Avinash,
• K. V. Sandeepa and
• T. Govindaraju

Beilstein J. Org. Chem. 2013, 9, 1565–1571, doi:10.3762/bjoc.9.178

• a stronger charge-transfer complex. Similar variations in the absorption spectra were observed for 2 in aqueous DMSO, while 3 exhibits only an incremental red shift of absorption maxima without any indication of the existence of two different (described above) kinds of aggregates as observed for 1

Presence or absence of a novel charge-transfer complex in the base-catalyzed hydrolysis of N-ethylbenzamide or ethyl benzoate

• Shinichi Yamabe,
• Wei Guan and
• Shigeyoshi Sakaki

Beilstein J. Org. Chem. 2013, 9, 185–196, doi:10.3762/bjoc.9.22

• rate-determining step of X = O is the first TS (TS1, the OH− addition step), while that of X = NH is TS2. TS2 of X = NH leads to a novel Mulliken charge-transfer complex, Ph–(OH)(O=)C∙∙∙N(H2)–Et. The superiority or inferiority between the direct nucleophilic process or the general base-catalyzed

Efficient, highly diastereoselective MS 4 Å-promoted one-pot, three-component synthesis of 2,6-disubstituted-4-tosyloxytetrahydropyrans via Prins cyclization

• Naseem Ahmed and
• Naveen Kumar Konduru

Beilstein J. Org. Chem. 2012, 8, 177–185, doi:10.3762/bjoc.8.19

• . Then, an intramolecular nucleophilic attack of the double bond in the oxo-carbenium ion led to cyclization and charge transfer complex formation with the tosylate group to afford the 2,6-disubstituted-4-tosyloxytetrahydropyran (Scheme 2). All structures of the 2,6-disubstituted-4

Anthracene appended pyridinium amide–urea conjugate in selective fluorometric sensing of L-N-acetylvaline salt

• Kumaresh Ghosh,
• Tanmay Sarkar and
• Asoke P. Chattopadhyay

Beilstein J. Org. Chem. 2010, 6, 1211–1218, doi:10.3762/bjoc.6.139

• exciplex or charge transfer complex in CH3CN is the key feature in the present study for the selective detection of a L-N-acetylvaline salt from other anionic guests. To explain the formation of an exciplex or charge transfer complex in 1 upon complexation of L-N-acetylvaline salt, compound 2 was

• -N-acetylvaline salt than with L-N-acetylalanine. This is attributed to the formation of a charge transfer complex between the excited state of anthracene and the electron deficient nitrophenyl urea during the interaction process. We believe that this characteristic feature with L-N-acetylvaline is