36358-10-8Relevant academic research and scientific papers
Dipolar cycloaddition reactions of nitrilimines
Dunstan, James B. F.,Elsey, Gordon M.,Russell, Richard A.,Paul Savage,Simpson, Gregory W.,Tiekink, Edward R. T.
, p. 499 - 509 (2007/10/03)
A series of γ-substituted α-methylidene-γ-butyrolactone derivatives underwent regiospecific 1,3-dipolar cycloaddition with N-methyl-C-phenylnitrilimine. These reactions proceeded regiospecifically and with high diastereoselectivity, generally favouring the anti diastereomer as determined by n.m.r, spectroscopy and semiempirical molecular orbital calculations. The assignment for one product was confirmed by X-ray crystallography. N-Methyl- C-phenylnitrilimine underwent regiospecific cycloaddition with a range of C=S-containing dipolarophiles. Substituted thioureas were generally unreactive as dipolarophiles, while 5-thio-substituted 1,3,4-thiadiazole-2(3H)-thiones underwent ready reaction to produce, rather than the expected cycloadducts, complex rearrangement products. The structure of one of these unusual products has been confirmed by X-ray crystallography. A series of disubstituted nitrilimines underwent regiospecific cycloaddition with thiobenzophenone; the structures of the products were confirmed by X-ray crystallography.
Thermal Cycloaddition Reactions of Thiocarbonyl Compounds. Part 2. 1,3-Dipolar Cycloaddition Reactions of Adamantanethione with Nitrile Oxides, Nitrilimines, and Diazoalkanes
Katada, Tomonori,Eguchi, Shoji,Sasaki, Tadashi
, p. 2641 - 2647 (2007/10/02)
1,3-Dipolar cycloaddition of adamantanethione (1) with nitrile oxides, nitrilimines, and diazoalkanes occurred smoothly to afford regioselective cycloadducts, adamantane-2-spiro-5'-(1',4',2'-oxathiazolines) (4a-f), adamantane-2-spiro-2'-(1',3',4'-thiadiazolines) (11a-d), and (21b), respectively in high yields.These results are discussed on the basis of FMO and steric effects.
