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28.9.1.1.1.1 Variation 1: Using Lead(IV) Acetate

DOI: 10.1055/sos-SD-028-00642

Carreño, M. C.; Ribagorda, M.Science of Synthesis, (200628630.

The oxidation of N,N-bis(organosulfonyl)benzene-1,4-diamines 9 with lead(IV) acetate was the first method used to synthesize benzo-1,4-quinone diimines (Scheme 3).[‌15‌] Glacial acetic acid is used as solvent and the procedure allows the synthesis of N-sulfonyl-protected imines, since the final quinone monoimine or diimine is stable under acidic conditions. For example, the reaction of 9 with lead(IV) acetate in acetic acid yields quinone diimines 10 by precipitation with ethylene glycol. A number of such diimines have been prepared following this method.[‌9‌,‌16‌] An aryl substituent at the sulfonyl moiety of 9 [R2=4-(R3HN)C6H4; R3=alkyl] can in turn support a 4-(aminoalkyl)phenyl group, which is unaffected under these reaction conditions.[‌17‌] Also reported is the reaction of N-(arylsulfonyl)-N-(2,4-dinitrophenyl)- or N-(alkylsulfonyl)-N-(2,4-dinitrophenyl)benzene-1,4-diamines 11 to give diimines 12 in good yields.[‌18‌] Quinone diimines bearing acyl and sulfonyl groups such as 14 are also available from the lead(IV) acetate oxidation of the precursors 13 in acetic acid.[‌19‌]

Meeeee 8 Meeeeeeee ee Meeee-8,8-eeeeeee Meeeeeee ee Meeeeeeee eeee Meee(MM) Meeeeee[‌8‌‌88‌]

Meeeeee eeeeeeee eee eeee ee eeee ee eeeee eeeeeeeeee, eee ee ee eeee eeeeeeeee ee eeeeee eee eeee(MM) eeeeeee ee eeeeee eeeeeee eeee. Meeeeeeee, eeeeee eee eeee eeee eeeee eeeeeeeeeeeee ee eeeeee eeeeeee eeeeeeee ee eeeeeee ee eee eeeeeee ee eeeee. Meee, e-eeeeeee eeeeeeee 88 eeee eeee eeee eeeeeeee ee eeeeeeeeee,[‌88‌] eeeeeeeeeeeeeee,[‌88‌] ee eeeeeee[‌88‌] eeeeeeeee eeee eee eeeeeee-8,8-eeeeeeee 88. Meeeeeeeee ee eeee eee eeeeeee ee eeeeee ee eeeeeeeeee eeeeeee eeeeeeee 88 eeee eee eeeeeeeeeeeee eeeeeee-8,8-eeeeeeee 88 eeeeeeeee ee eeeeee ee [(eeeeeeeeeeeeee)eeeee]eeeeeeee eeeeee, ee eeeeeeeee eeeeee (Meeeee 8).[‌88‌] Mee eeeeeeeee eeeeeeeeeee eeeeeeee ee eee eeeeeeee eeee ee 88 ee eeeeeeeeee ee Meeeee eeeeeeee eeee eee 8-eeeee-eeeeeeeee eeeeeee-8,8-eeeeeee, eee ee eee eeeeeeee eeeee eee eeeeeeeee eeeeeeeeee.

Meee eeeeee ee eeee eeee ee eeeeeeeeee eeeee-8,8-eeeeeee eeeeeeeeee. Meee, eee eeeee-eeeeeeeee eeeeeee eeeeeeeee 88 eee eeee eeeeeeee eeee 8,8,8,8-eeeeeeeeeee-M,M-eeeeeeeeeeeeee-8,8-eeeeeee (88) eeee eee eeee(MM) eeeeeee eeeeeeeee ee eeeeeeee ee eeeeeee eeeeeeeee (Meeeee 8).[‌88‌] Mee eeeee ee eeee eeeeeeeeeeeeee ee eee eeeeeeee. Meeeeeeeeeee, eee eeee eeeeeee eeeeeeeee ee eeeeeee eeeeeeeeee eeeeee ee eee eeeeeeeee ee eeeeeeeeeeeee eeeeeeeeeee 8-eeeeeeeeeeee. M eeeeee ee eeeeeeeeeee eeeee- eee eeeeeee-eeeeeeeeeee 8-eeeeeeeeeeee eeee ee 88, eeeeeee eee eeeee eeeeeeee ee ee (eeeeeeeeeeee)eeeeeeeeeeeee, eee eeeeeeee eeeeeeee ee eeeeeee eeeeeeeeee 88 eeeee eeee(MM) eeeeeee ee eeeeee eeee eeeeeeee,[‌88‌] eeee eeeeee eeeeeee eeee 88 ee 88%. Mee eeeeeeee eee eeeeeeeeee ee eee eeeeeeeee eeeeeeeeeeeee 88 ee eeeeeeee eeee eee eeeeeeee eeeeee eeeeeeee ee eeeeeeeee ee eeee eee eeeeeee-eeeeeeeeeee 88. Mee eeeeeeeee ee eee eeeee eeeeeeee ee eee ee eeeee eeeeeeeee eeeeeeeeeee. Mee eeeee eeeee eee ee eeeeeeeee eeeeee ee ee eeeee ee e eeeeeeeeeee. Meee eeeeee eeeeee eee eeeeeeeeeeee eeeeeeeee ee 88 eeeeeeee eeee eee eeeeeee 88.[‌88‌] Meeeeeeee e eeeeeee eeeeeeeee, eeee(MM) eeeeeee eeeeeeeee ee eee 8-eeeeeeeeeee eeeeeeee 88 ee eee M,M-eeeeeeeeeeeeeeee-8,8-eeeeeeee 88 eeeee ee eee e-eeeeeee eeeeeeeee 88[‌88‌] ee eeeeeeee 88.[‌88‌,‌88‌]

Meeeee 8 Meeeeeeee ee Meeeeee Meeeeeeeee eee Meeeeeee ee Meeeeeeee eeee Meee(MM) Meeeeee[‌88‌‌88‌]

Meeeeeeeeeeeeeeeeeeeee eee eeeee eeeeeeeeeeeeee eeeeeeeeeee eeee eeee eeee ee eeeeeeeeee eeeeee ee 8-eeeeeeeeeeeeeee eee eeeee eeeeeeeeeeeeee eeee eeeeeee eeeeee.[‌88‌] Meee eee eeeeeeeee ee 88 eeee eeee(MM) eeeeeee ee eeeeeeee ee eeee eeeeeeeeeeeeeee, e eeeeeee ee eeeeeee eeeeeeeee 88 (88% eeeeeeee eeeee), eeeeeee eeeeeeeee eeeeeeee eeeeee 88 (88%), eee eeeeeeeeeeeee 88 (88%) ee eeeeee (Meeeee 8). Meee eeeeeeee ee eeeee ee eee eeeeeeeeeeeeeee eeeeeeee, eee eeeeee 88 eee ee eeeeeeee ee 88% eeeee, eee eeee e eeeee ee 88 eee 8% ee 88 eee eeeeee. Me eeeee ee eeeee, 88 eeeeeee eee eeeee eeeeeeeee ee eee eeeeeeee eeeeeee eee eee ee eeeeeeee eeee ee 88% eeeee.

Meeeee 8 Meeeeeeeeeeeeeeeeeeeee-Meeeeeeee 8-Meeeeeeeeeeeeee ee Meeeeeeeee ee Meeeeee Meeeeeeeee[‌88‌]

Meeeeeeeeee 8

Meeeeee Meee Meeee (%)88 Meeee (%)88 Meeee (%)88 eee
MM8Me8 8e 88 88 88 [‌88‌]
MM8Me8/MeMM 8eee eeeee 88 8 [‌88‌]
MM8Me8/M8M 8e 88 88 88 [‌88‌]

Mee eeeeeeee ee ee M-eeee-eeeeeeeeeeeeee eeeeeeeeee eeeee ee eeeeeeeeee ee eeeeeeeee eee eeeee eeeeeee eeeeeeeee 88 eeee eeee(MM) eeeeeee eeeeeeeee ee M-(eeee-eeeeeeeeeeeeee)-8-eeeeeee-8-(8-eeeeeeeeeeeee)eeeeeee (88) ee eeeeeeeeeeeeeee.[‌88‌] Me eeee eeee, eee eee ee eeeeee eeeeeeeeee ee eeeeeeeee eeeee ee eee eeeeeeeee eeeeeeeeee eeeee ee eee eeeeeee eeeeeeeee 88. Meeeeeee 88 ee eeeeeeeee eeee M-(eeee-eeeeeeeeeeeeee)-8-eeeeeeeeeeeeee (88) eeeeeee eeeeeeeeeeeeee eeeee-eeeeeeee eeeeeeeeee eeeeeeee ee eee eeeeeeee ee ee-8-eeeee eeeeeeeee eee eeeeeeeeee eeeeeeeeee eeeeeeeee ee eee eeeeeeeee eeeeeee eeee 8-eeeeeeeeeeeeeeeeeee eeee. Meeeeeeee, eeeeeeeee eeee eeee(MM) eeeeeee eeeeee eee eee ee eeeeeee-eeeeeeeeeee eeeeeeee, eeeeeee ee eeee eeeeeee, ee eeeeeeeeee ee eee eeeeeeeeeeeee eeeeeee eeeeee, eeeeeeeeeeee eeeee eeeeeeeeeeee ee eeeeeeeee eeeeeeeeeeee ee eee eeeeeeee eeee (Meeeee 8).

Meeeee 8 Meee(MM) Meeeeee Meeeeeeee ee e eeee-Meeeeeeeeeeeee-Meeeeeeee 8-Meeeeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

M8-(Meeeeeeeeee)-8-eeeeee-M8-(eeeeeeeeeeeeee)eeeeeeeee-8,8-eeeee-8,8-eeeeeee (88, M8=Me; M8=M; M8=Me; M8=MM8Me); Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeeeeee ee 88 (M8=Me; M8=M; M8=Me; M8=MM8Me; 8.8e, 88eeee) ee eee MMMe8 (MeMM eeeeeee; 888eM) eee eeeee eee ee eeee eeeeee eeeeeee eee Me(MMe)8 (88.8e, 88eeee). Meeee eeeeeeeeeee eeeeeeee eee eeeeeeeee eeeeeeeeee ee ee eee 8e, eee eeeeeeeee Me eeeee eeee eeeeeee ee eeeeeeeeee. Me eee eeeeeeee eee eeeee eeeeeeeee eeeee (88888°M; 88eM) eee eee eeeeee eee eeeeeee ee eeeeeeeeeeeee 88eM eeeee eeeeeee eeeeeeee. Meee eeeeeee ee eee eee, e eeeee eeeeeeee ee eeeeee eeeeeeee eeeeee. Meeeeee eeeeeee ee eeeeeee eeeeeeee ee eeeeeee ee eee eee eeeeeeee eeeeeeeeee eeeee ee eeeeee eeeee; eeeee eeeee: 8.8e (88%); eeeeeeeeeeeeeeeee (Me8M ee MMMe8/Me8M) eeeeeeee eee eeee eeeeeee.

References


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