Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines

• Matthew J. Fleming and
• David M. Hodgson

Beilstein J. Org. Chem. 2021, 17, 2385–2389, doi:10.3762/bjoc.17.155

• carbenoids may compete with a desired carbenoid transformation although its value has been demonstrated in, for example, our studies on lithium 2,2,6,6-tetramethylpiperidide (1, LTMP)-induced syntheses of 2-ene-1,4-diols and 2-ene-1,4-diamines from terminal epoxides [3] and aziridines [4][5], respectively

Gram-scale preparation of negative-type liquid crystals with a CF₂CF₂-carbocycle unit via an improved short-step synthetic protocol

• Tatsuya Kumon,
• Shohei Hashishita,
• Takumi Kida,
• Shigeyuki Yamada,
• Takashi Ishihara and
• Tsutomu Konno

Beilstein J. Org. Chem. 2018, 14, 148–154, doi:10.3762/bjoc.14.10

• to the LC display industry. The stereochemistry in the ring-closing metathesis step 5→4 was determined as follows. As depicted in Table 2, it has been generally recognized that the melting points of trans-1,4-disubstituted cyclohexane-1,4-diols are much higher than those of the corresponding cis

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

Anionic sigmatropic-electrocyclic-Chugaev cascades: accessing 12-aryl-5-(methylthiocarbonylthio)tetracenes and a related anthra[2,3-b]thiophene

• Laurence Burroughs,
• John Ritchie,
• Mkhethwa Ngwenya,
• Dilfaraz Khan,
• William Lewis and
• Simon Woodward

Beilstein J. Org. Chem. 2015, 11, 273–279, doi:10.3762/bjoc.11.31

• Laurence Burroughs John Ritchie Mkhethwa Ngwenya Dilfaraz Khan William Lewis Simon Woodward School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom 10.3762/bjoc.11.31 Abstract 1,4-Diols resulting from the double addition of ArCCLi (Ar = Ph

Copper-catalyzed aerobic aliphatic C–H oxygenation with hydroperoxides

• Pei Chui Too,
• Ya Lin Tnay and
• Shunsuke Chiba

Beilstein J. Org. Chem. 2013, 9, 1217–1225, doi:10.3762/bjoc.9.138

• aerobic oxygenation of aliphatic C–H bonds with hydroperoxides, which proceeds by 1,5-H radical shift of putative oxygen-centered radicals (O-radicals) derived from hydroperoxides followed by trapping of the resulting carbon-centered radicals with molecular oxygen. Keywords: copper; 1,4-diols; free

• could be trapped by O2 to form the new C–O bonds. Herein, we report the realization of this concept mainly for the aerobic synthesis of 1,4-diols from hydroperoxides, which could be catalyzed by the Cu(OAc)2-1,10-phenanthroline system in the presence of Et3N as a terminal reductant of the Cu(II) species

• present aerobic strategy for the synthesis of 1,4-diols by targeting methylene C–H oxygenation with various tertiary hydroperoxides 1 (Table 2). Generally, oxygenation of benzylic methylene C–H bonds proceeded smoothly to give the corresponding 1,4-diols 3 in good to moderate yields (77–51% yields) (Table

Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives

• Filipe Vilela,
• Peter J. Skabara,
• Christopher R. Mason,
• Thomas D. J. Westgate,
• Asun Luquin,
• Simon J. Coles and
• Michael B. Hursthouse

Beilstein J. Org. Chem. 2010, 6, 1002–1014, doi:10.3762/bjoc.6.113

• –carbon or carbon–hydrogen bonds followed by formation of new ones via alkyl, hydride and allylic shifts. However, one cannot assume that the mechanism is pinacol-like. Saturated 1,4-diols favour the formation of tetrahydrofuran derivatives, whilst allylic cations will involve some degree of stabilisation

Systematic investigations on the reduction of 4-aryl-4-oxoesters to 1-aryl-1,4-butanediols with methanolic sodium borohydride

• Subrata Kumar Chaudhuri,
• Manabendra Saha,
• Amit Saha and
• Sanjay Bhar

Beilstein J. Org. Chem. 2010, 6, 748–755, doi:10.3762/bjoc.6.94

• -oxoester to 1,4-diols was finally established (Scheme 11) when substrate 14 [40] (incapable of lactonization due to distal spatial disposition of the oxo- and methoxycarbonyl moieties imposed by the rigidity of the cyclopropane ring system) underwent selective reduction of the oxo-functionality only under