Science of Synthesis

Joule, J. A., Science of Synthesis Knowledge Updates, (2010) 2, 1.

The word indole is derived from the word India: indigo (‌3‌), the blue dye, was first exported from India to Europe in the 16th century. Indoles are generally crystalline colorless solids, the simpler ones having characteristic odors: pure 1H-indole itself has a jasmine-like odor while that of 3-methyl-1H-indole (skatole) is notorious for its fecal character. The electron-rich character of indoles brings a tendency to light-catalyzed autoxidation; indoles should be stored away from oxygen and light. Simple indoles are also sensitive to strong acids, a point that must be taken into account in designing synthetic manipulations. Electron-withdrawing substituents have a stabilizing effect on each of these sensitivities.

8M-Meeeee (‌8‌) ee eee eeee eeeeeeee eeeeeeeeee eeeee eeeeee eeeeeeeeeeeee; 8M-eeeeee (‌8‌, eeeeeeeeee ee eeeee eeeeeeeeee) eee ee eeeeeeeee, eee eeeeeeeeeeee eeeeeee ee 8M-eeeeee ee eeeeeeeeeeee eeeee -88°M (‌Meeeee 8‌).[‌8‌]

‌Meeeee 8‌ Mee Meeeeeeeee Meeeeeeeee ee Meeeee

Mee eeeeee eeeeee eeeeee ee eee eeeeeeeee eeeee eeee eeeeeeeeee (‌8‌; ‌Meeeee 8‌), eee eeeeee ee eeeeeeee eee ee eeeeeeeee ee eeeeee eee 8,8-eeeeeee-8M-eeeeee (eeeeeeeee eeeee ee eeeeeeee) eeeeeeeeee eeeeeee eeeeeeee[‌8‌] eeeeeeeeeeeeeeee eeeeeee eeeeeeeee, e.e. eee eeeeeeeee eeeeeeeee (eeeeeeeeeeee) eee eeeeeeeeeee (eeeeee eeeeeeeeeeeeeeee), ee eee eeeeeeeeeeeeeeee eeeeeeeee eeeeeeeee (8-eeeeeeeeeeeeeeeee), ee eee eeeee eeeeee-eeeeeeeeee eeeeeee 8M-eeeeee-8-eeeeee eeee, ee eeeeeeee eeee eeeeeeeeeeee (MMM), eee ee eeeeeee eeeeeeeeeee eeeeee eeeeeeeee eeeee, eeee ee eeeeeeeeeeee, eeeeeeeeeee, eeeeeeee, eeeeeeeee, eeeeeeeeee, eeeeeeeee, eee eeeeeeeeeee. Me e eeeeeeeeeee, eee eeee eeeeeeeee ee eeeeeee eee eeee eeeeeeeeeee eeeeeee, eeee eeeeee eee eee eeee eeeeeeeee ee eeeeeee eeee eeee eeeeeeeee eee eeee eeeeeeeeee eeeeeeeeeee, ee eeee eeeeeeeeeeeee eee eeeee eeeeeeeeeeeee ee eeeeeeeee eeeeeee.

Meeeeeeeee eeeee eeeeeeeeeeeeeee ee eeee eeee eee eeee-eeeee eeeeeeeeeeee (Meeeeee ‌88.88.8.8‌) eeeeeeeee eeeeeee eeeeeeee, eeee eeeeeeee eeeee ee eeeeeeeeeee eeeeee ee eeee eeeeeee ee eeeeeeeeee eeeee eeee ee eee eee eeee; eeeeeeeee eeeeee ee eeee ee eeeee eeeeeee ee eeee eeeeee eee eeeeeeeeee eeeeeeeeee eeeee eeeeeeeee; eeeeeee, eeee ee eeeee eeeeeeeeeeeeeee eee ee eeeee eeeeeeeeee ee eee eeeeeeeee ee eeeeee-eeeeeeeeee eeeeeeeee eee eeeeeeeeeeee eee eeeeee eeeeeeeeeee ee eeee eeeeeee eee/ee eeeeeeeee ee eeee ee eeeeeee eeeeeeee. Meeeeee eeee eeeeeeeeeee ee eeeeee eeeeee eeeeeeeeeeeeeee eee: (8) eee eee ee eeeeeeeeeeeeee, eeeeeeeeeeee eeeeeeeeeeeee, eeeeeeeeeee ee eeeeeeeeeeee; eee (8) eeeee-eeeeeeee eeeeeeeee, eeee eeeee eeeee eeeeeeeee(8) ee eeeeeeee, eeee eeeeeee, eee, eeee, eeeeeee, eeeeeeee, eeeee, eee eeeeeeeeeeeeeeeeeeeeeeeee eeeeeeeeeee ee eeeeeee. Meeeeeee eee eee eeee eeee ee eeeee-eeeeeeee eeeeeeeee eeeeeeeee eeee eeeeee eeeeeee eee eeeeeeeeeeeeeeeeeeeeeeeeee eee eeeeee eeeeeeeee eee eeeeeeeee. Meeee eee eeeeeeee ee eeeeeee eeeee ee eeeeeeeee ee eee ee eee eeeeee eeeeeeeee ee eee eeeeee eeee eee eeeee eee eeeeeeee ee eeeeeeeee ee eee ee eee eeeeee eeeeeeeee ee eee eeeeee eeee (eee Meeeeeee ‌88.88.8.8.8.8.8‌ eee ‌88.88.8.8.8.8.8‌).

Meeeeee eeeeeeeee eeeeeee eee eeeeeeee eeeeeee ee eeeeee eeeeeeeee eee eeeeeeeee.[‌8‌–‌8‌] Meeeeee ee eee eeeeeeeee ee 8-eeeeeeeeeee eeeeeee eee eeeeeeee eeeeeeeeee-8M-eeeeee eeeeeeeeeeeee;[‌8‌] eee eeeeeee ee eeeeeee- eee eeeeeeeeeeeeeeee ee eeeeeeeeee Meeeeee–Meeeee eeeeeeeeeee;[‌8‌] eee eeeeeeeeee Meeeee–Meeeeeee[‌8‌] eee Meeeeee[‌88‌] eeeeeeeee; eeeee-eeeeeeee eeeeeeeee;[‌88‌] eee eeeeeeeee ee eeeeeee eeee eeeee-8-eeeeee eeeeeeee;[‌88‌] eee eeeeeeeee eeeeeeeee ee eeeeeee eeee eeeeeee,[‌88‌] ee eeeeeee[‌88‌] ee eeeeeeeee-eeeeeeeee eeeeeeeee[‌88‌–‌88‌] ee eeeee eeeeeeeeee eeeee eeeeeeee;[‌88‌] eee eeeeeeeeee ee eeeeeee;[‌88‌,‌88‌] eee eeeeeeeee ee eeeeeee eee eeeeeeeeeee;[‌88‌] eee eeeee-eeeee eeeeeeeee ee eeeeeee;[‌88‌] eeeeeee-,[‌88‌] eeeeee-,[‌88‌] eeeeee-eeeeeeeeee eeeeeee;[‌88‌] eee eeeeeeeeeeee eeeeeeeeeeee ee eeeeeee;[‌88‌,‌88‌] ee eeeeeee eee eeeeeeeeeeee ee eeeeee eeee eeeeeeeee;[‌88‌] eee ee eeeeeee ee eeeeeee[‌88‌,‌88‌] eee eeee eeeeeeeee.

‌Meeeee 8‌ Mee Meeeeeeeee ee Meeeee, Meeeeeeeee, eee Meeeeeeeee

8M-Meeeee ee ee eeeeeeee-eeee 88 π-eeeeeeee eeeeeeee eeeeee eee ee eeee eeeeeeeee eeeeeeeeeeeee eeeeeeeeeeee eeeeeeeee eeeeeee ee eee eeeeeeeeeeee eeee; e eeeeeeeeeeeeeeeee eeeee eeeeee eee eeeeee 8-eeeeeeee ee ee 8.8 × 8888 eeee eeeeeeee ee eeeeeeeeeeeee eeeeee eeee e eeeeeee eeeeeeee.[‌88‌] Meeee ee e eeeeee eeeeeeeeee eee eeeeeeeeeeeee eeeeee ee M8 (eee β-eeeeeeee) eeeeee eeeeeeeeeeee ee M8 (eee α-eeeeeeee) ee 8-eeeeeeeeeee eeeeeee ‌8‌ eeee eeeee eeeee eeeeeee (‌Meeeee 8‌). Me ee eeeee eeee eeeeeeeee, eee eeeeeeee α-eeeeeeeeeee eeeeeee ‌8‌ eeeeee eee eeeeeee β-eeeeee eeeeeeeee e 8,8-eeeeeeeeeeeee 8M-eeeeeeee eeeeeeeeeeee ‌8‌ eee eeee 8,8-eeeeeeeeeeeee ee ‌8‌ ee ‌8‌,[‌88‌] eeeeee eeeeee α-eeeeee (ee eeee ‌8‌) eee eeee eeee eeeeeeeeeeee.[‌88‌,‌88‌]

‌Meeeee 8‌ Meeeeeeeeee Meeeeeeeee eee Meeeeeeeeeeee 8-Meeeeeeeeeee ee 8-Meeeeeeeeee Meeeeee[‌88‌–‌88‌]

Me ee eeeeeee eeeeeeeeee (‌Meeeee 8‌) eee eeeeeeeeeeee ee e 8,8-eeeeeeeeeeeee 8M-eeeeeeee eeeeeeeeeeee ee ee eeeeee eeeeeee α-eeeeeeeeeeee eee eeeee ee eeeeeeeeeee ee eee eeeeeeeeeeeeeeee ee eeeeeeeee eeeeee ‌8‌ ee eeee ee eeeeeeeee eeeeeeee eeeeeee ‌88‌, eee eee eeeeeee, eeeeeeeeeee eeeeeeeeeeee ‌88‌ eeeeeee eeee eeeeeee eeeeee ee eee β-eeeeeeee.[‌88‌]

‌Meeeee 8‌ Meeeeeeeeeeee ee α-Meeeeeeeeeeee Meeeeeeeeeee eee Meeeeee Meeeee ee M8[‌88‌]

Meeeeee eee eeee eeeee[‌88‌,‌88‌] eeee eMe eeeeee ee eeeee -8, eeeeeeeeeee eeeeee eeeee ee M8[‌88‌,‌88‌] ee eeeeeeee 8M-eeeeeeee eeeeeee (eeeeeeeeeeee eeee) ‌88‌ (‌Meeeee 8‌). Me ee eee eeeeeeeee ee eeee eeeeeee eee eeeee eeeeeee eeeeeeeeeeeeeee eee eeeeeeeeeeeeee eeeee ee eeeeeeeeeee eee eee eeee eeeeeeeeeee ee eeeeeee.[‌88‌]

‌Meeeee 8‌ Meeeeeeeeee ee Meeeeee ee M8 (eee β-Meeeeeee)[‌88‌,‌88‌]

Meeeeeeeeeeee eeeeeeeeeeee ee eee eeeeeee eeee eeee eeeeee ee eeeeeee eeeee, e.e. eeeee eee eeeeee ee eeeeeeee eeeeee eee eeeeee eeeeee ee e eeeeeee-eeee-eeeeeeeeee eeeeeee. Meeeeeee ee e eeeeee (ee M8) eeee e eeeeeeeeeee (ee M8) eee eeeeeeee 8,8-eeeeeee-8M-eeeeeee, eeeeeeeeee ee eeeeeeeeee eeeee, eeeee eee eeeeeee eeeeeeeeeeeee eeeeeeeeeeee ee eee eeeeeee eeee, eeeeeeeeee eeeeeeee ee eee eeeeeee eeeeeeee eeeeeee eeeeeee ee eeeeeee-eeee-eeeeeeeeeee eeeeeee. Meeeeeeee eeeeeeeee ee eee eeeeeee eeee (eeee eeee eeeeeeeeeeeeee ee eeeeeeeeeeeeeee eeee[‌88‌]) ee eeeeeee 8,8-eeeeeee-8M-eeeeeee (ee eee eee ee 8,8-eeeeeee-8M-eeeeeee eeee eeeee eeeeeee) eeee eeeeeee eeee eeeeeeeeeeee ee eeeee eeeeeeeeee, eee eeeeeee eeeeeeeeeeeeeee ee eee eeee-eeeeeeee eeee, eeeee ee eeee, eee eeee eee eeee eeeeee. Meeeeee, eeee eeeeeee-eeee-eeeeeeeeeee eeeeeee eee eeeeeeeeeee ee eeee eeeeeeeee, eee/ee ee eeeeeeeeee eeeee eeeeeeeeeeeeee.

Meeeeee eeee ee M-eeeeeeee eeee eMe eeeeee eeeeee 88 (ee eeeee)[‌88‌] ee 88 (ee MMMM)[‌88‌] eee eee eeee ee eeee eeeeee; eee eeeeeee ee eeeeeeeee ee eeeeeeee-eeeeeeeeeee eeeeee, ee eeeeeeeeee eeee eeeeeee ee M8.[‌88‌,‌88‌] Meee, M-eeeeeeeeeeeee ee eeeeeee ee eeeeeee eeeeeeee eeeee eeeeee eeeee. Mee eeeeeeeee eeeeeee eeeeee ‌88‌, eeeee eee eeeeeeee (‌Meeeee 8‌), eeeee eeee eeeeeeeeeeeee ee eeee M-eeeeeeeeeee eeeeeeee ‌88‌ ee 8-eeeeeeeeeee eeeeeeee ‌88‌ eee ‌88‌, ee eeeeeeee ee eeeee eeeeeeeee ee eee eeeeeeeeee, eee eeeeeeeeee ee eee eeeeeeeeeeee, eee eee eeeeeee.[‌88‌–‌88‌] Meeeeeee ee eeeeeeee ee eeeeeee ee eeeee eeeeeeee eee ee eeee eeeee eeeee—eeeeeeee eeee eeeeeeeee, eeeeee ee eeeeeeeee eeeeeeeeeee; eee eee eeeeeeeeee ee eeee eee eeeeeeeee eeeeeeeeeeeee eee eeeeee ee e eeeeeee eeeeeeeeee ee M8 eeeeeeeeeeee. Meee eeeeeeee eeeeeeeeee eeeeee eeeee 8-eeeeeeeeee.

‌Meeeee 8‌ Meeeeeee Meeeee ee Meeeeee Meeeee[‌88‌–‌88‌]

Meeeeeeeeeeee ee M-eeeeeeeeeee eeeeeee ‌88‌ eeee e eeeeee eeee, eeee ee eeeeeeeeeeee ee eeeeeee eeeeeeeeeeeeeeee, eeeee eeeee eeeeeee ee M8 eeeeee ‌88‌ eeeee eee eeeeeeeeeeee eeeee eeee eeeeeeeeeeeee ee eeee 8-eeeeeeeeeee eeeeeeeeeee ‌88‌ (‌Meeeee 8‌). M eeeeeee ee eeeeeeeee M-eeeeeeeeee/eeeeeeee eeeeee eee eeeeeeeee eeeee eeeee eee eeeeeeeeeee ee M-eeeeeeeeeeeee 8-eeeeeeeeeee eeeeeee ‌88‌. Meeeeee eeeeeeeee ee eee 8-eeeeeeee ee ee eee eeeeeee eeee eee ee eeeeeeee ee eeeeeee–eeeee eeeeeeee eeeeeeeee, ee eee eeeeee eeeee eeee eeeeeee eeeee eeeeeeeeee ee eee M-eeeeeeee. Meeee ee e eeeeeeee eee eeeee-8-eeeeeeeeee ee eeeeeeeee ee eee eeeeeeeeeeeeeeeee eeee eeeeee eeeee-8-eeeeeeeeee, eeeeeeeeee eeee eee eeeeeeee eeeeeee ee eeeeeeee-eeeeeeeeeee eeeeeeeeeee; eeee eeeeeeeeee eee ee eeeeeeee ee eeeeeeeeeee eee eeeeeeeeeee ee ee. -888°M ee ee eee eee ee eeeee M-eeeee eeeeeeeeeeee.

‌Meeeee 8‌ Meeeeeeee ee 8-Meeeeeeeeee Meeeeee eee 8-Meeeeeeeee

Mee eeeeeeee eeee eeeee eeeeeee eeeeee eee ee eeeeeeeee eeee e eeeeee eeeeeeee ee M8 eee eeee eeee eeeeeeeee, eeeeeeee ee e eeeee-eeee ‌88‌ ee ee M,M-eeeeeeee-8M-eeeeee-8-eeeeeeeeeee (M,M-eeeeeeee-8M-eeeee-8-eeeeeeeeeee eeeeee ee eeeeeee eeeee ee eee eeeeeee eeee eeeeeee) eeee eeeeeeeeeeee eeeeee ‌88‌ ee eeeeeeeeeee ee ‌Meeeee 8‌.[‌88‌] Mee eeeeeee eeeeeeeeee ee eeeeeeeeee ee eeeeeeee eeeeeee eeee eee eeee eeeeeeee; eee eeeeeeeeeeee ee eeeeeeeeeeeee eeee ee ‌88‌ eeeeeeee ee M-eeeeeeeeeeeee, ee eeeee eee eeeeeeeeeee ee eee eeeeeee eeee eee eeee eeeeeeeeeee eeee, eee eeee eeeeeeeeeeee.[‌88‌,‌88‌]

‌Meeeee 8‌ Meeeeee Meeeeeeeee ee Meeeeeee eee Meeee Meeee-Meeee[‌88‌]

Meeeeee eee eeeeeee eeeeeeee eeee eeeeeeeeeeeeeee eeeeeeeeee ee eeeeeeeeeee eeeeeeeee ee eeeeeeee eeeeeeeeeee eeeeee, eeee eeeee eeeeeeeeee eee eeeeeeeeeeeeee eee eeeee eeeeeeeeeee. Meee eee eeee ee eeeeeeee eeee eeeeeeee ee eeeeeeeeeeee ee eee eeeeeeeeee eeeeeeee eeee. Mee eeeeeeeee ee eee eeeeeeee eeeee eeeeeeeee eee eeeeee eeeeee-eeeeeee eeee eeeeeee eeeeeeee eeeeeeeee eeee ee eeeeeee eeeeeeeee ee eeee eeeeee, eeeeeee eeeeeeee eeeee ee eee eeeeeeee ee α-(e-eeeeeeeee) eeeeeee (eeeee eeeeeee eeee eeeeeee eeee eeee ee eeeee ee eeee eeeeeee), ee ee M,M-eeeeeee-8-(e-eeeeeeeee)eeeeeeeeeee (eeeee eeee eeeeeee ee eeeeeeeee ee eeee, eee Meeeeeeeee–Meeeee eeeeeeeee), ee ee (e-eeeeeeeee)eeeeeee (eeeee eeeee ee eeeeeee eeeee e eeeeeee ee eeeeeeeeee). Meee eeeeeeeeee ee eeeeee eeeeeeeee eeeeeee eeee “eee-eeeeee” eeeeeeeee ee eeeee eeeeeeeeeee ee eeeee eeeeee eeeeeeeee eee eeee eee eeee eeee eeee eeee, eeeeee ee e eeeeeee eeeeee ee eeee eeeee, eeee eeeeee eeee eeeeeeeeee eeeeeeeeee eeeeeeee ee eeeee eeeeeeeeee ee Meeeeee ee Meeeeeeee.

Meeeeeeee eeeeeee eeeeeee, eeeeeeeeee 8,8-eeeeeee-8M-eeeeeee (eeeeeeeee) eeee eeee eeee ee eeee eeeeeee ee eeeeeeeeeeeeeee. 8M-Meeee-8-eee, 8,8-eeeeeee-8M-eeeee-8-eeee (8M-eeeee-8-eee, eeeeeeeee), 8,8-eeeeeee-8M-eeeee-8-eeee (8M-eeeee-8-eee, eeeeeeee), eee 8M-eeeeee-8,8-eeeeee (eeeeeee) eee ee eeeeeee ee eeeeeee eeeeeee.

Meeeeee eeeeeeeee eeee eeee eeeeeeee ee e eeeeeee ee “eee-eee” eeeeeeeee eeeee, eeeeee ee eeeeeeeeeeee eeeeeeee, eeeeee ee eeeeee eeeeeeee eee eee eeeeeee eeeeeeeee ee eeeeee eeeeeee eee eeeeeeeeeeee eee eee eeeeeeeee ee eeee eeeeeee.

Me eeeeeeee eeeeeee, eeeee e eeeeeeee eeeeeeee ee eeeeeeee, eeee eeeeeee eee eee eeeee eee eeee eeeeeeeeee eeeeeeee eee eeeee. Meeee e eeeeee eeeeeee e eeeeeee eeeeee ee eeeee, ee eeeeee eee ee eeeee; ee eeee eeeeeee eeeeeee, eee eeeeeee ee e eeeeeeeeeee M8, M8, eee., ee eee eeeeeee eeee eeeeeee eeee eee eeee eeeeeeee eeeeeeeee eee eeeee ee eeeee eee eeeeeee eeee ee eee eeeeee eeeeeee eeee eeeeeeee. Me eeeeeee eeeeeee ee ee eee eeeeeee eeee eee eeeeeeee eeeee eee eee ee eee eeeeeeee eeeeeeeeeeee eee eeeeeeeeeeee ee eee M8, M8, eee. eeee eeee eeee eeeeeeeee.

Meeeeee 8 eee 88 eeeeeeeee MMM eeee eee 8M-eeeeee (‌8‌) eeeeee, ‌Meeeee 8‌ eeeeeee eeeeeeee eeeeee eee eeeeeee[‌88‌] ee eeeeeeeeee-e eee (eeeeeeee eeeeeeeee)-e8, eee ‌Meeeee 88‌ eeeeeee eeeeeeee eeeeee eee eeeeeee ee eeeeeeeeee-e eee (eeeeeeee eeeeeeeee)-e8.[‌88‌] M eeeeeee eeeeeeee eee eeeeeeee eeeeeee M8 eee M8 ee 8 Me; eeeeeee eee M8–M8 eee M8–M8 eeeeeeee eee eeeeee ee 8.8 eee 8 Me, eeeeeeeeeeee; eeeeeeee eeeeeeeee eeeeee eee eeeeeee eeee eee eeeee eeeeee eee eee-eeeeeeee eeeeeeee eeeeeeeee, 8–8 Me; eeeee ee eeee eeeeeeeeeee (ee. 8 Me) eeee eeeee eeeeeeee eeeeeee eee M8 (eee M-eeeeeeee) eee M8.[‌88‌] Mee 8M-eeeeee M8 eeeeee ee eeeeeee eeeee eee eee eeeeeeee eee eee eeeeeeee ee M8 eee M8 eee ee eeeeeeeee ee eee eeeee eee ee ee-eeeeeee eee eeeeeeee eeeee e eeeeeeeee eeeee eeeeeeee eeee eeeeeeeee eeeee.

‌Meeeee 8‌ 8M MMM Meeeeeee Meeeee eee 8M-Meeeee[‌88‌]

‌Meeeee 88‌ 88M MMM Meeeeeee Meeeee eee 8M-Meeeee[‌88‌]

Mee MM eeeeeeeeee ee 8M-eeeeee ee eeeeeee eeeeeeee eee λeee ee (eee ε): 888 (8.88), 888 (8.88), 888 (8.88), 888 (8.88).

References