82817-41-2Relevant academic research and scientific papers
SPIROADAMANTYL STABILIZATION OF SULFUR-SUBSTITUTED 1,2-DIOXETANES
Adam, Waldemar,Arias, Luis A.,Scheutzow, Dieter
, p. 2835 - 2836 (1982)
With the help of spiroadamantyl substitution, the first sulfur-substituted 1,2-dioxetanes 9 and 10, respectively derived from thiophenylmethyleneadamantane (7) and 2-adamantylidene-1,3-dithian (8) were prepared via singlet oxygenation and detected by NMR.
The Synthesis of Spirodioxetanes>
Adam, Waldemar,Encarnacion, Luis A. Arias
, p. 2592 - 2605 (2007/10/02)
It is shown that the spiroadamantane group stabilizes thermally labile 1,2-dioxetanes sufficiently to permit isolation.With the help of this stabilizing group it was possible to prepare the first sulfur substituted dioxetanes 9k and l and characterize them by low temperature 13C and 1H NMR spectra.Photosensitized singlet oxygenation at low temperature, using either polymer-bound Rose-Bengal or tetraphenylporphyrin as sensitizer in methylene chloride, of the corresponding 2-methyleneadamantanes 8 was the method of choice for the preparation of the spirodioxetanes> 9, provided that the methylene carbon bears no alkyl or phenyl substituents.The Kopecky method, i. e. hydroperoxybromination of the 2-methyleneadamantanes 8 and subsequent dehydrobromination, proved unsuccessful to prepare the dioxetanes 9.
