Science of Synthesis

Rück-Braun, K.; Priewisch, B., Science of Synthesis, (2007) 31, 1349.

The Fischer–Hepp rearrangement of secondary N-nitrosoanilines ‌82‌ to C-nitrosoanilines ‌83‌ (‌Scheme 41‌)[‌123‌] occurs in the presence of hydrogen chloride in organic solvents such as alcohols, diethyl ether, or chloroform. Such reactions may also be run as “single-pot” processes, without the need to handle the starting N-nitrosoanilines, since the latter can usually be preformed by the nitrosation of a secondary aniline and used directly.[‌124‌] In general, only para-nitrosylated anilines ‌83‌, as their hydrochlorides, are isolated from the rearrangement, although the formation of minor amounts of ortho-rearranged compounds may be observed by careful examination.[‌125‌] The mechanism of the rearrangement has been the subject of debate and evidence has been put forward in favor of either an inter- or an intramolecular reaction.[‌126‌]

‌Meeeee 88‌ Meeeeee–Meee Meeeeeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeee-M-eeeeeeeeeeeee (‌88‌, M8 = Me):[‌888‌]

M 8 M-eeeee eeeeeeee eeee e eeeeeeeeee eeeeeee, e eeeeeeeeeee, eee e eee-eeeee eeee eee eeeeeee eeee eeeeeee (888 e), M-eeeeeeeeeeeee (888 e, 8.8 eee), eee e eeee ee MeMM8 (88 e, 8.8 eee) ee M8M (888 eM). 88.8% ee M8MM8 (888.8 e) eee eeee eeeee eeeeeeee eeee e eeeeee ee 88 eee. Mee eeeeeeeeeee ee eee eeeeeee eee eeeeeee ee eeee ee 88°M eee ee eee eeee ee eeee eeeee eee ee eeeeeeeeee 88 eee. Mee eeeeeee eeeee eee eeee eeeeeeeee eeee eee eeeeeee eee eeeeeeeee, eeeeeee eee eeeeeeeeeee ee eee eeeeeee eeeee eeee eeeeeeeee eee M-eeeeeeeeeeeeee ‌88‌ (M8 = Me), eee eeeeeeee ee 88–88°M eee MMe(e) (88.8 e, 8.8 eee) eee eeeeee eeeeeee eeee ee eeee e eeeeee ee 8 e, eeeee eeeeeeee eee eeeeeee eee eeeeeee. Mee eeeeeeeeeeeee eeee ee eee eeeee eeeeeeee eeeee ee eeeeeeee ee e eeeee-eee eeeee eee eee eeeeee eee eeeeeee eee e eeeeeee 8 e ee 88–88°M. Me eee eee ee eeee eeee 88% ee MeMM eee eeeee ee eeeeee eee eM ee eee eeeeee ee 8–8 eeeee eeeeeeee eeeeeee ee eeeeee eee eeeeeeeeeee eee eee eeee eeeee 88–88°M. Mee eeeeeee eee eeeeeee ee 88–88°M eee 88 eee, eee eeee eeeeee ee 88–88°M. Mee eM eee eeeeeeeeee ee 8.8 ee eee eeeeeeee ee 88% ee MeMM. Meeee eeeeeee eee eeeeeeeeeee ee eee eeeeeee ee 88–88°M, eee eeeeee eeee eeeeeeeee. Mee eeeeeee eeeee eee eeee eeeeeeeee ee 8°M. Mee eeeeee-eeeee eeeeeeee eeee eee eeeeee eeee eeeeeeeee ee eeeeeeeeee, eeeeee eeee eeeeee, eee eee eeeee ee 88°M eeeeeeeee; eeeee: 888 e (88%); ee 888–888°M.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8, 8888.
• 8.Meeeee-Meee, (8888) M 88e8, 888.