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 Variation 1: Wittig Reactions of (α-Halomethylene)phosphoranes

DOI: 10.1055/sos-SD-043-00383

Sankararaman, S.Science of Synthesis, (200843454.

A one-pot conversion of an aldehyde into the corresponding terminal acetylene is possible by the use of ylides obtained from (halomethyl)phosphonium salts 51 and (halomethyl)phosphonates. The procedure involves a Wittig reaction leading to the formation of a vinyl halide 52, followed by a 1,2-elimination of hydrogen halide to yield the terminal alkyne 53 (Scheme 30).[‌54‌,‌55‌] For a related method, see also Scheme 14, Section

Meeeee 88 Meeeee Meeeeeee ee (Meeeeeeeeeeee)eeeeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeee 88

M8 M Meeeeeeeee Meeee (%) Mee
8-eeeeeee Me 8. MeMe, MMM, ee
8. MeMM8, eee MM8, 88°M
88 [‌88‌]
Me 8. MeMe, MMM, ee
8. MeMM8, eee MM8, 88°M
88 [‌88‌]
Me e-MeMM, MMM, eeeeee 88e [‌88‌]

e Mee eeeeeeee eeeeeeee ee e eeeeeeeeee; eee eeeeeee ee e eeeee.

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeeee (88, M8=8-Meeeeee); Meeeeee Meeeeeeee:[‌88‌]

M 8.88M eeee ee MeMe ee Me8M (88.8eM, 8.88eee,) eee eeeee ee e eeeeeeeeee ee (eeeeeeeeeeee)eeeeeeeeeeeeeeeeeeee eeeeeeee (88, M=Me; 88.8e, 8.88eee) ee Me8M eeee 88eee ee 88°M. Meeee eeeeeeee eee 88eee, e eeee ee eeeeeeeeee-8-eeeeeeeeeeee (8.88e, 8.88eee) ee MMM (888eM) eee eeeee eee eee eeeeeee eee eeeeeee eeeeeeeee ee ee. Mee eeeeeee eee eeee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eeee eeeeeee eee eeeeeeeee ee eeeeeee (888eM) (MMMMMMM: eeeeeeeeee). Mee eeeeeee eeee eee eeeeee eeeeeee e eeeee eeeeee ee eeeeeee (88e), eee eeeeeeee eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeeeeee ee eeeeeee (88eM) eee eeeee eeeeee eeeeeee e eeeee ee eeeeeee (88e). Mee eeeee eeeeee eeeeee eeeeeeee ee eee eeeeeeeeeeeee ee eee eeeeeeee eee eeeeeeeee ee MMM (88eM) eee eeeee eeee 88eee ee e eeeeeeeeee ee MeMM8 [eeeeeeee eeee Me (8e, 8.88eee)] ee eee MM8 (888eM) eeeeeeeeee ee 88°M. Meeee 8e, eee MM8 eee eeeeeee ee eeeeeeeee eee e eee. MM8Me eeee eee eeeee ee eee eeeeeee eeeee eeeeeee eeee eee eeeee. Meeee eeeeeee ee eee eeeeeee eeeeeee eee M8M eeeee eeeeeee eeeeeeee, eee eeeeeee eee eeeeeeeee eeee Me8M (888eM). Meeeeeeeeeeee ee eee eeeeeee eeee ee eeee eeeeeeee, eeeee eee eeeeeeeee ee eeeeeee (88eM) eee eeeeee eeeeeee e eeeee eeeeee ee eeeeeee (88e). Mee eeee eeeeeee eeeeeeee eeee eeeeeeeeeeeee ee eee eeeeeeee eee eeeeeeeee ee eeeeeeeee eeeee (ee 8888°M) eee eeeeeee ee eeeee ee ee, eeeeeeeee Me8MM eeeeeeeeeeee. Mee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee eee eee eeeeeeee eee eeeeee eeeeeee e eeeee eee ee eeeeeee (88e) ee eeeee eee eeeee eeeeeee, eeeee eee eeeeeeeeeeeeee (eeeeeeeee eeeee) ee eeeeee eeeee eeeeee eeeeeeee; eeeee: 88%; ee 8888.8°M.

8,8-Meeeeeeee[8.8]eeeeeeeeeeeeee (88, M8=[8.8]Meeeeeeeeeeeee-8,8-eeee); Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee eeeeeeeeeee eeee 88 (M=Me; 8.88e, 88.8eeee) ee MMM (88eM) eee eeeee e-MeMM (8.88e, 88.8eeee) ee eee eeeeeee, eeee eeeeeeee, ee 88°M. Mee eeeeeeeeee eee eeeeeee ee 88°M eee 88eee, eee e eeee ee 8,8-eeeeeeee[8.8]eeeeeeeeeeeeee (8.88e, 8.8eeee) ee MMM (88eM) eee eeeee eeee 88eee. Mee eeeeeee eee eeeeeee ee eeee ee ee eee eeeeeee eee e eeeeeee 8e. Meeeeee eeeeeee ee e-MeMM (8.88e, 88.8eeee) eee eeeee eee eee eeeeeee eee eeeeeeee eee 8.88e. Meeee eeeeeeee ee ee eeeeeeeee, M8M eee eeeee, eeeeeeee ee eee. ee MM8Me eee eeeeeeeeeeeeee. Mee eeeeeee eeeee eee eeeeeeeee, eeeeee eeee 8M MMe eee eeeee, eee eeeee (MeMM8). Mee eeeeeee eeeeeeee eeeee eeeeeee ee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/eeeeeee 8:8) ee eeee eeeeeeeee eeeeeeee; eeeee: 8.88e (88%); ee 888°M.