39755-31-2Relevant articles and documents
Cyclophanes. 14. Synthesis, Structure Assignment, and Conformational Properties of (2,5)Oxazolo- and Thiazolophanes
Mashraqui, Sabir H.,Keehn, Philip M.
, p. 4461 - 4465 (1982)
The first synthesis of cyclophanes containing aromatic nuclei with two heteroatoms is described.A Hoffman pyrolytic route was used.Two isomeric (2,5)oxazolophanes (6a and 6b) and two isomeric (2,5)thiazolophanes (13a and 13b) were isolated.In both cases the isomers were found to have the anti-anti and the anti-syn structure.The assignments were made by spectral analysis and variable-temperature nuclear magnetic resonance spectroscopy in the oxazolophane case and on the basis of NMR spectral comparisons between normal (13a and 13b) and deuterated derivatives (14a and 14b) in the thiazolophane case.While the aromatic nuclei in the thiazolophanes were found to be conformationally rigid on the NMR time scale, those in the oxazolophanes were found to be conformationally mobile with a rotational barrier of 17.8 kcal/mol.
Unexpected rearrangements of rhodium carbenoids containing a pyrrolidin-1-yl group
Diehl, Julian,Brückner, Reinhard
supporting information, p. 2629 - 2632 (2014/05/06)
Ketone- and ester-substituted diazo compounds, which contain a pyrrolidine moiety were treated with dirhodium tetraacetate generating the corresponding rhodium carbenoids. They were expected to insert into a CH bond of the pyrrolidine moiety but reacted differently. The ketone-substituted rhodium carbenoid underwent a Wolff rearrangement. The resulting ketene continued to react by lactamization and electrocyclic ring-opening and gave an acrylamide. The ester-substituted rhodium carbenoid underwent a [1.2]-shift of the (pyrrolidin-1-yl)methyl moiety, which resulted in a methacrylic ester. For each rearrangement a mechanism is suggested.
Efficient routes to isotopically labelled epichlorohydrins ((chloromethyl) oxiranes)
O'Hagan,White,Jones
, p. 871 - 880 (2007/10/02)
Efficient routes are developed for the synthesis of variously labelled 2H- and 13C- labelled epichlorohydrins prepared from appropriately labelled acetic acids and sodium borodeuteride. The route is versatile and can be used for strategic location of isotopes at C-I, C-2 and C-3 of epichlorohydrin. By way of demonstration [2-13C]-, [2-2H]-, [3-2H2] and [2-2H, 3-2H2]-epithlorohydrins have been prepared. In addition the syntheses can be adapted for the preparation of enantiomerically pure and isotopically labelled epichlorohydrins.