Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
25.6.6.10 Method 10: The Gattermann Reaction

DOI: 10.1055/sos-SD-025-00443

Schall, A.; Reiser, O.Science of Synthesis, (200725636.

Chloroiminium salts 36, generated by addition of gaseous hydrogen chloride to anhydrous hydrogen cyanide in the presence of aluminum trichloride or zinc(II) chloride, are highly reactive formylating reagents (Scheme 20). This process, known as the Gatterman reaction, is especially useful for the formylation of phenols and hetarenes (Table 17);[‌4‌] however, in contrast to the VilsmeierHaack reaction, discussed in Section 25.6.6.4, aromatic amines are not compatible substrates. In return, already weakly activated benzenes such as xylenes can be formylated in good yields (Table 16). The isolation of the resulting aldehydes in pure form is especially facile, because the aldiminium salt 37 often precipitates from the reaction mixture and can then be isolated by simple filtration and subsequently hydrolyzed to give the aromatic aldehyde.

Meeeeeeeeee, eeeeee eeeeeee eee ee eeeeeeee ee eeeeeeeeeeee ee eeee eeeeeee ee eeeeeeee eeeeeee (MeeeeeMeeeee eeeeeeeeeeee).[‌888‌]

Meeeee 88 Mee Meeeeeeeee Meeeeeee[‌8‌]

Meeee 88 Meeeeeeeee Meeeeeeeeee ee Meeeeeeeeee Meeeeeeeeeeee[‌88‌,‌888‌‌888‌]

Meeee Me8 Meeeeeee Meeee (%) Mee
8 8,8-Me8M8M8 MMe, MMM, MeMe8 88 [‌888‌]
8 8,8-Me8M8M8 MMe, MMM, MeMe8 88 [‌888‌]
8 8-MMM8M8 MMe, MMM, MeMe8 88 [‌888‌,‌888‌]
8 8-MeMM8M8 MMe, Me(MM)8, MeMe8 88 [‌888‌,‌888‌]
8 MMe, Me(MM)8, MeMe8 88 [‌888‌]
8 MMe, Me(MM)8 88 [‌888‌]
8 MMe, Me(MM)8, MeMe8 88 [‌888‌]
8 Mee MMe, Me(MM)8, MeMe8 8888 [‌888‌]
8 MMe, MMM, Me(MM)8 88 [‌888‌]
88 MMe, Me(MM)8, MeMe8 88 [‌88‌]
88 MMM, MeMe8, MMe 88888 [‌888‌]

Meeee 88 Meeeeeeeee Meeeeeeeeee ee Meeeeeeeee Meeeee eee Meeeeeeee[‌888‌,‌888‌‌888‌]

Meeee Meeeeeeee Meeeeeee Meeee (%) Mee
8 MMe, Me(MM)8 88 [‌888‌]
8 MMe, MMM, MeMe8 88 [‌888‌,‌888‌]
8 MMe, MMM, MeMe8 88 [‌888‌]
8 MMe, MMM, MMMe8 88 [‌888‌]
8 MMe, MMM, Me8M 88 [‌888‌]
8 MMe, MMM, MeMe8 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeee-8,8-eeeeeeeeeeeeeeeeeeee (Meeee 88, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

MMMMMMM: Meeeeeee eeeeeeeeeee eeee ee e eeeeee eeeeeeee ee eee eeeeeee eee eeeeee eeeeeeeee eeee eeeee.

8,8-Meeeeeeeeeeeeee (88.8e, 8.888eee) eee eeeee ee eeeeeeeeeeeeeeeee (888eM) eee eeeeeeeeee ee 88°M. Me(MM)8 (88.8e, 8.888eee) eee eeeee, eee MMe(e) eee eeeeeee eeeeeee eee eeeeeee eeee eeeeeeee. Mee eeee ee MMe(e) eeeeeeee eee eeeeeeee ee eeeee eee MMe eeeeeeeeee. Meeee 8e ee MMe(e) eeeeeeee, eee eeee ee eeeeeeeeee eeeeeeeeeeeee eeeeeeeee eee MeMe8 (88.8e, 8.888eee) eee eeeee. M eeee eeee ee MMe(e) eeee eee eeeeeeeeee. Mee eeeeeeeeeee eee eeeeeeeee ee 88°M eee eeeeeeeeee ee eeee eeeee eee 8e. Mee eeeeeee eee eeee eeeeee eeee e eeeeeee ee eee (888eM) eee eeeee MMe (888eM). Mee eeeeeeee ee eee eeeeeeee eeeeee eeee eeee eeeeee eeee MMMe8 (8×888eM) eee eeeee ee eee eeeeeee eeeee. Mee eeeeeeeee eeeeeeee eeeee eee eeeeeee ee 8888°M eeeeeeeee. Mee eeeeeee eeeee eee eeeeeeeee eee eee eeeeeee eeeee eee eeeeee eeee MMMe8 (888eM eee 888eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee eeeeeeeee M8M (8×888eM), eee eee eeeeeee eeeeeeee eeee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeeeee eee eeeeeeeeeee ee e eeeeeeeeeeee eeeee eeeeeeee eeee e Meeeeee eeeeee eee eeeeeeeee (888°M/8.8Meee) ee eeee e eeeeeeeeee (88.8e) eeeeeeeeee eeeeeeee eeeeeeeeeeeeeeeee eee e 8:8 eeeeeee ee eee eeeeeee 8-eeeeeee-8,8-eeeeeeeeeeeeeeeeeeee eee 8-eeeeeee-8,8-eeeeeeeeeeeeeeeeeeee. Mee eeeeeeeeee eee eeeee ee e-MeMMe eee eeeeeeeeeeee eeeeeeeee ee 8°M. Mee eeeeeeee eeee eeeeeeeee ee eeeeeeeeee eee eeeeee eeee MeMMe/eeeeee (8:88, 8eM) ee eeee 8-eeeeeee-8,8-eeeeeeeeeeeeeeeeeeee (8.88e). Mee eeeeee eeeeee eee eeeeeeeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:88) ee eeee ee eeeeeeeeee 88.88e; eeeee: 88.88e (88%).

8-Meeeeee-8-eeeeeeeeeeeeeeeeee (Meeee 88, Meeee 88); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeee eee ee eeeeeeeee eeeee.

MMMMMMM: Meeeeeee eeeeeeeeeee eeee ee e eeeeee eeeeeeee ee eee eeeeeee eee eeeeee eeeeeeeee eeee eeeee.

MMe(e) eee eeeeee eee 88eee eeeeeee e eeeeeee ee eeeee MMM (88e, 8.88eee) eee 8-eeeeeeeeeeeee (88e, 8.88eee) eeeeee ee ee eee eeee. MeMe8 (88e. 8.88eee) eee eeeee eeeeeeeee. Meeee eeeeee eeeeee eeee MMe, eee eeeeeeeeeee eee eeeeee ee 88°M eee eeeeeeeeee eee 88e. Mee eeeeeee eee eeeeee eeee eee eee MMe. Mee eeeeeeeee eeeeeeeeeee eee eeeeeeee ee MMe. Mee eeeeeeee eee eeeee eeeeeeeee eee eeee eeeeeee eeee MeMMM8 eeee. Mee eeeeeeeee eeeeeeee eeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeee eeee ee Me8MM8. Mee eeeeeeee eee eeeeeeee ee e eeeeeeeee eee; eeeee: 8888e (88888%); ee 888°M.

References


Cookie-Einstellungen