A new, single-mode bench-top resonator was evaluated for the microwave-assisted flow generation of primary ketenes by thermal decomposition of α-diazoketones at high temperature. A number of amides and β-lactams were obtained by ketene generation in situ and reaction with amines and imines, respectively, in good to excellent yields. The preferential formation of trans-configured β-lactams was observed during the [2+2] Staudinger cycloaddition of a range of ketenes with different imines under controlled reaction conditions. Some insights into the mechanism of this reaction at high temperature are reported, and a new web-based molecular viewer, which takes advantage from Augmented Reality (AR) technology, is also described for a faster interpretation of computed data.
Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff-Staudinger Cascade Reaction / Musio, B.; Mariani, F.; Sliwinski, E. P.; Kabeshov, M. A.; Odajima, H.; Ley, S. V.. - In: SYNTHESIS. - ISSN 0039-7881. - 48:20(2016), pp. 3515-3526. [10.1055/s-0035-1562579]
Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff-Staudinger Cascade Reaction
Musio B.;
2016-01-01
Abstract
A new, single-mode bench-top resonator was evaluated for the microwave-assisted flow generation of primary ketenes by thermal decomposition of α-diazoketones at high temperature. A number of amides and β-lactams were obtained by ketene generation in situ and reaction with amines and imines, respectively, in good to excellent yields. The preferential formation of trans-configured β-lactams was observed during the [2+2] Staudinger cycloaddition of a range of ketenes with different imines under controlled reaction conditions. Some insights into the mechanism of this reaction at high temperature are reported, and a new web-based molecular viewer, which takes advantage from Augmented Reality (AR) technology, is also described for a faster interpretation of computed data.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
