"The photochemical decomposition of diphenyldiazomethane in the presence on N-sulfinylamines leads to ketimines. By-products include tetraphenylethylene, benzophenone, thiobenzophenone, and benzophenone azine. This reaction is the first example of carbene addition to a non-carbon containing multiple bond system. Evidence indicates that the carbene adds to the N=S bond of the N-sulfinylamine to give the corresponding thiaziridine-S-oxide which spontaneously decomposes to give ketimine and SO. In the dark N-sulfinylaniline catalyzes the decomposition of diazoalkanes to carbenes. This decomposition presumably takes place through a thiatriazole-1-oxide intermediate. The carbene then reacts either with N-sulfinylaniline to form ketimine, after loss of SO, or with diazoalkane to give olefin"--Abstract, page iii.
Stoffer, James O.
Hanna, Samir B.
Russell, Robert R.
Mayhan, Kenneth G.
McDonald, H. O. (Hector O.)
Ph. D. in Chemistry
National Science Foundation (U.S.)
University of Missouri--Rolla. Department of Chemistry
University of Missouri--Rolla
ix, 72 pages
© 1970 Harry Robert Musser, All rights reserved.
Dissertation - Open Access
Library of Congress Subject Headings
Carbenes (Methylene compounds)
Print OCLC #
Electronic OCLC #
Link to Catalog Recordhttp://laurel.lso.missouri.edu/record=b1066940~S5
Musser, Harry R., "The reaction of N-sulfinylamines with diazoalkanes" (1970). Doctoral Dissertations. 2303.