In:
Synthesis, Georg Thieme Verlag KG, Vol. 54, No. 24 ( 2022-12), p. 5423-5433
Abstract:
A general strategy for the synthesis of 2-substituted cyclobutanone sulfides via a tandem Brønsted acid-catalyzed nucleophile addition/ring contraction/C3-C4 ring expansion reaction sequence has been exploited. The procedure led to a wide panel of four-membered cyclic ketones in good to excellent yields and with broad substrate scope. Mechanistic aspects and kinetic parameters were investigated by quantum chemical DFT calculations, allowing us to rationalize the different reactivity of 2-aryl- and 2-alkyl-substituted 2-hydroxycyclobutanones towards thiol nucleophiles in reactions mediated by sulfonic acids. NMR and in situ Raman techniques were employed to better understand the reaction kinetics and parameters that affect the desired outcome.
Type of Medium:
Online Resource
ISSN:
0039-7881
,
1437-210X
Language:
English
Publisher:
Georg Thieme Verlag KG
Publication Date:
2022
detail.hit.zdb_id:
204080-3
detail.hit.zdb_id:
2033062-5
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