Conformational equilibria of six-membered ring sulphoxides: the effect of β-electron-withdrawing groups

Bergesen, Knut; Carden, Brian M.; Cook, Michael J.

doi:10.1039/p29780001001

Cited by 9 publications

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“…The sulfoxide was prepared using general procedure A for the synthesis of sulfoxides: pale yellow solid (0.38 g, 67%), which was used without further purification: mp 84–85 °C (lit . 85–88 °C); ν max (neat)/cm –1 1715 (CO); δ H (400 MHz) 2.26–2.36 (1H, m, one of C H 2 ), 2.51–2.64 (2H, m, C H 2 ), 2.78–2.94 (1H, m, one of C H 2 ), 2.95–3.05 (1H, m, one of C H 2 ), 3.08–3.16 (1H, m, one of C H 2 ), 3.63 (1H, A of AB q , J 13.3, one of C H 2 ), 3.69 (1H, B of AB q , J 13.3, one of C H 2 ); δ C (75.5 MHz) 19.3, 41.4, 46.7, 59.8, 199.7; m / z (ESI+) 133 [(M + H) + , 30)].…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of Cyclic α-Diazo-β-keto Sulfoxides in Batch and Continuous Flow

et al. 2017

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Diazo transfer to β-keto sulfoxides to form stable isolable α-diazo-β-keto sulfoxides has been achieved for the first time. Both monocyclic and benzofused ketone derived β-keto sulfoxides were successfully explored as substrates for diazo transfer. Use of continuous flow leads to isolation of the desired compounds in enhanced yields relative to standard batch conditions, with short reaction times, increased safety profile, and potential to scale up.

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Section: Methodsmentioning

confidence: 99%

“…Found: C, 45.06; H, 6.14; S, 23.94. Spectral details in agreement with those reported in the literature …”

Section: Methodsmentioning

confidence: 99%