Science of Synthesis

Joule, J. A., Science of Synthesis Knowledge Updates, (2010) 2, 39.

The hydroformylation of monosubstituted alkenes can lead to aldehydes by attachment to either the terminal or substituted carbon; however, conditions are available to introduce the carbon monoxide exclusively to the terminal, unsubstituted carbon.[‌179‌] By carrying out the hydroformylation process in the presence of an arylhydrazine, direct formation of an aldehyde arylhydrazone results and the Fischer sequence then ensues, producing a one-pot sequence to the 3-substituted indole ‌120‌, from the alkene (‌Scheme 45‌).[‌180‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeee eee Meeeeeeeeeeeeeee ee Meeeeee ee eee Meeeeeee ee Meeeeeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Mee eeeeeeeeeeee ee eeee eeeeeeee, eeeeeeeee eee eeeeeee ee eeeee eee eee eeeeeeee ee eeeee, ee eeeeeeeeeee ee eee eeeeeeeeeee ee e eeeeeee ee eeeeeeeeee eeeeeeeee ‌888‌, ee eeeeeeeeeee ee ‌Meeeee 88‌.[‌888‌,‌888‌]

‌Meeeee 88‌ Meeeeeeeeee eee Meeeeeeee Meeeeeee eee Meeeeeeeeeeeeeee ee Meeeeee[‌888‌,‌888‌]

‌Meeeeeeeeee 88‌

M8	M8	M8	Meeee (%)	Mee
M	M	MM8MMe8	888	[‌888‌]
M	M		88	[‌888‌]
M	M		88	[‌888‌]
M	M		88	[‌888‌]
M	M		88	[‌888‌]
M	M	MMMeM(Me)Me	88 (M) + 88 (M)	[‌888‌]
	Mee	(MM8)8MMe8	88	[‌888‌]
	Mee		88	[‌888‌]
	Mee		88	[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeee-8-eeeeee-8M-eeeeee (‌888‌, M8 = M; M8 = Me; M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.

M Meee eeeeeeeee eeeee eeeeeeeee (888 eM) eee eeeeeee eeee Me(eeee)(MM)8 (8.8 eee%), 8,8′-eee{eee[8,8-eee(eeeeeeeeeeeeeee)eeeeee]eeeeeeeee}eeeeeeee (Meeee; 8.8 eee%), eeee-8-eee (88.8 eeee), (8-eeeeeeeeeeee)eeeeeeeee (88.8 eeee), eee eeeeeee (88 eM) eeeee eeeee. Mee eeeeeeeee eee eeeeeeeeeee eeee MM (8 eee) eee M8 (8 eee) eee eee eeeeeeee eee eeeeeee eee ee 88°M eee 88 e. Mee eeeeeeeee eee eeeeee ee ee eee eeeeeeeeeeeee. Mee eeeeeee eee eeeeeeeeeee ee e Meeeeee eeeee eeeee eeeee eee eeeee (MeMM8), eee eeee MeMe8 (88 eeee) eee eeeee eee eee eeeeeee eee eeeeee eeeee eee eeeeeeee eee eeeeeeee; eeeee: 88%.

8-Meeeee-M-[8-(8-eeeeeeeeeeeeeee-8-ee)-8M-eeeee-8-ee]eeeeeeeee (‌888‌, M8 = 8-MM8M8MMMM; M8 = 8-Meeeeeeeeeeeeee-8-ee); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.

8-Meeeee-8-eeeeeeeeeeeeeeeeeee (888 ee, 8.88 eeee), eeee-eeeee M-[8-(8-eeeeeeeeeeeeeeeeee)eeeeee]eeeeeeeeeeeeeeeeeeee (888 ee, 8.88 eeee), Me(eeee)(MM)8 (8.8 ee, 8 eee%), eee MMMMM (88 ee, 8 eee%) ee M8MM8 (8.8 e, 8 ee% ee M8M, 8.8 ee% eeeeee) eeee eeeee ee ee eeeeeeeee eeeee eee eeeeeeeeeee eeee M8 (88 eee) eee MM (88 eee). Meeee eeeeeeee eee eeeeeee eee 8 e (eeee e eeeeeee eeee eeeee eee eee eeeee eee eee eeeeee eeeee eeeeeeeeeee, eee eeeeeeee eeee eee ee eeeeeee eeeeeee) ee 888°M, MM8 (88 eM, 88 ee% ee M8M) eee eeeee, eee eee eeeeeee eee eeeeeeeee eeee MeMMe. Mee eeeeeee eee eeeeeee ee eeee eee eeeeeee eeeeeee eeeeeee eeeeeeeeeeee; eeeee: 888 ee (88%).

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