Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
10.13.1.1.1.3.1.1.5 Variation 5: From Alkenes via Hydroformylation

DOI: 10.1055/sos-SD-110-00001

Joule, J. A.Science of Synthesis Knowledge Updates, (2010239.

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

M8 M8 M8 Meeee (%) Mee
M M Me 88 [‌888‌]
M M MM8MMe 88 [‌888‌]
Me M Me 88 [‌888‌]
M Me Me 88 [‌888‌]
Me M Me 88 [‌888‌]

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%).

References