- Structure and thermal reactivity of some 2-substituted 1,3-oxathiolane S-oxides
-
Isomerization of 2-benzylidene-1,3-dioxolane to 3-phenylbutyrolactone occurs readily under flash vacuum pyrolysis (FVP) conditions. 2-Diphenylmethyl-1,3-oxathiolane and 2-benzyl-1,3-oxathiolane have been prepared and the latter compound has been oxidized to the corresponding sulfoxide, whose structure and conformation are examined by 1H NMR, and to the sulfone whose X-ray structure is determined. 2-Benzylidene-1,3-oxathiolane is also prepared and the behavior of the three S-oxidized oxathiolane derivatives upon FVP is examined. While extrusion of SOn to give ethene and a carbonyl compound predominates in all three cases, the sulfoxide gives also bis(2-hydroxyethyl) disulfide, most likely formed via thiirane S-oxide and 1,2-oxathietane.
- Aitken, R. Alan,Henderson, Sarah,Slawin, Alexandra M. Z.
-
p. 422 - 434
(2018/03/26)
-
- Photochemical Synthesis of 4-Oxobutanal Acetals and of 2-Hydroxycyclobutanone Ketals
-
Irradiation of α,β-unsaturated ketones (aliphatic, both open chain and cyclic as well as aryl substituted) in 1,3-dioxolane in the presence of a sensitizer (benzophenone or anthraquinone) led to 4-oxobutanal acetals in fair to excellent yield through a very simple procedure (workup in most cases by bulb-to-bulb distillation). The resulting acetals were irradiated to give 2-hydroxycyclobutanone ketals, again through a simple procedure that gave a good yield with open-chain aliphatic derivatives.
- Manfrotto, Cristina,Mella, Mariella,Freccero, Mauro,Fagnoni, Maurizio,Albini, Angelo
-
p. 5024 - 5028
(2007/10/03)
-