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34.1.4.2.8.1 Variation 1: In Combination with Organic Bases (Amines or Ethers)

DOI: 10.1055/sos-SD-034-00041

Dax, K.Science of Synthesis, (200534138.

From the combinations of hydrogen fluoride with organic bases, 70% hydrogen fluoride/pyridine (234) [pyridinium poly(hydrogen fluoride)] provides an efficient means to convert alcohols into the corresponding fluoroalkanes.[‌250‌‌252‌] It is sometimes called Olah's reagent, and is commercially available. Nevertheless, a procedure for its synthesis[‌252‌,‌253‌] is reproduced below (Scheme 49). A selection of results with alcohols is presented in Table 29.

Meeeee 88 Meeeeeeee ee 88% Meeeeeee Meeeeeee/Meeeeeee[‌888‌,‌888‌]

Meeee 88 Meeeeeeee ee Meeeeeeeeeeee Meeee 88% Meeeeeee Meeeeeee/Meeeeeee[‌888‌,‌888‌]

Meeeeeeee Meeeeeeeeee Meeeeee Meeee (%) Mee
Me8MMM MM, eeeeee, 8°M, 8.8e Me8MM 88 [‌888‌]
e-MeMM MM, eeeeee, 88°M, 8e e-MeM 88 [‌888‌]
MeMM MM, eeeeee, 88°M, 8e MeM 88 [‌888‌]
e-MeMM8MM MM,e 88°M, 8e e-MeMM8MM 88 [‌888‌]

e Meeee eeeeee ee 88% eeeeeeee eeeeeeee/eeeeeeee; MM=eeeeeee eeeeeeee.

e MeM (8.8 eeeee) eeeeeee ee eeeeee eeeeeee eeeee ee eeeeeeee ee eeeeeeeee.

Meeeeeee eeeeeeee eeeee eeeeeee eeee 88% eeeeeeee eeeeeeee/eeeeeeee ee eee eeeeeeeeeeee eeeeeee eeeee eeeeeee ee eeeeeeeeeee eee/ee eeeeeeeeeeeee; eee eeeee ee eeeeeeee eeeeeeeeee ee eeeeeeeee. M eeeeeee eeeeeee ee eeeee ee Meeeee 88 eeee eee eeeeeeeee ee 8-eeeeee­eeeeeeeeee[‌888‌] (888) eeee eeeeeeeee-8-ee (888). Meeeeeeee eeeeeeeeee eeee e eeeee eeeeeeee eeee eee eeee eee eeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeee, eee eeeeeeeee eeeee, eeeeee; eeeeee-8-ee eeeeeeee e 88% eeeee ee 8-eeeeeeeeeeeee eeee, eeeee 8-eeeeeeeeeeee (888) eee ee eeeeeeeeeee ee 88% eeeee (Meeeee 88). Mee eeeeeeeee ee eeeeeeeeeeeeeeeee eeee eeeeeeeeeeee ee eeeeeeee ee ee eeeeeeeeeeee; eeee ee ee eeeeeeeeeee eeeeee ee eee eeeee eeeeeeee eeeeeeeee ee eee eeee eeeeeeeeeeeee eeeeee eeeeeeeeeee eeeeeee ee eeeeeeeeeeee. Meeeeee eeeeeeee eeeeee eeeeeeeeeeeeeeeeeeeee ee eeee 88% eeeeeeee eeeeeeee/eeeeeeee, eee eeeee ee eeeeeeee eeeee eeeeeee eeeeeeeeeeeee eeee ee eeeeee eeeeeeee ee eeeee ee eee eeeeeeee eeeeeee.[‌888‌]

Meeeee 88 Meeeeeeee ee 8-Meeeeeeeeeeeeeee eee 8-Meeeeeeeeeee Meeee Meeeeeee Meeeeeee/Meeeeeee[‌888‌,‌888‌]

Me eeeeeeee ee eeeeeeeee eeeeeeee eeeeeeee, 88% eeeeeeee eeeeeeee/eeeeeeee ee eeeeeeee ee eeeee eee ee MM8-eeee eeeeeeeee.[‌888‌] Meeeee eeeeeeeee ee eeeeeeeeeeeee ee eeeeeeee eeee eeeeeeeeee eeeee eee eeeeeee eeeee ee eeeeeee ee e eeeeeeeeeee eeeeee. Meeeeee, eee 8α-eeeeee eeeeeeeeee eee eee eeeeeee ee eeeeeeeeeee eee eeeeee eeee eee eeeeeeee ee eeeeeee ee 8α- ee 88β-eeeeeee eeeeeeee. Meee, eeeeeeeee ee eeeeeeeeeeeee ee eee eeeee eeee eee eeeeeee eeeee ee eee eeeeee eeee eeeeeeee ee eee eeeeeeeee eeeeeeeeee.[‌888‌] Meeeeeeee ee e 8,8-eeeeee-8-eeeeeeeeeee-8-ee eeee 88% eeeeeeee eeeeeeee/eeeeeeee eeeeee (M8/M8) eeee eeeee eeeeeeee ee eeeeeeeeeeeeee MeeeeeeMeeeee eeeeeeeeeee eeeeeee eee eeee eeeeeeeee eeeeeeeee eeeeeee eeeeeeeeeeee eeee eeeeeee eeee M,M-eeeeeeeeeeeeeeeeee eeeeeeeeeee ee Meeeeeee'e eeeeeee.[‌88‌]

Meeeeeeeeeee ee Meee'e eeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeee eee eeeeeeeee eeeeeeee eeeeeeee (ee eeeeeeeeeeeee ee eeeeeee) eeeeee eeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeeeee eeee 8-eeeeeeeee-8-eeee[‌888‌] eee eeeeeeeeeeeeeeeeee,[‌888‌] eeeeeeeeeeee. Me eeeee eeeeeeeee eeee eeee eeee eeeeeeeeee eeeeee e eeeeee eeeeeeeeeee ee e eeeeeee eeeeeeee, eee eeeeeeeee ee eeeeeeee ee ee Meeeeee 88.8

Mee eeeeeeee eeeeeeeeeee eeee eee eeeeeeee, eeeeee, eee eeeeeeee ee eeeeeeeee eeeee 88% eeeeeeee eeeeeeee/eeeeeeee eee ee eee eeeeeeeeeee ee eeeee eeee(8-eeeeeeeeeeeee eeeeeeeeeeeeeeeee).[‌888‌,‌888‌] Me ee eeeeeeeeeeee eeeeeeeee, eee eee ee eeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeee eeeeeeee ee eeee-eeeee eeee(8-eeeeeeeeeeeee) ee 88°M.[‌888‌] Me e eeeeeeee eeeeeeee eeeeeee ee 88%, eeee eeeeeee eeeeeee eeeeeeeeeee eeeeeeee eeeeeeee. Mee eeeeeeeeeeeee eeeeeeeeeeee ee eeeeeeee ee 8888% eeeee ee eeeeeeee e eeeeeee ee eeeeeeeee eee eeee(8-eeeeeeeeeeeee eeeeeeeeeeeeeeeee) ee eeeeeeeeeeeeeee ee eeee eeeeeeeeeee eee 8eeeee. Me eee eeeeeeee eeee eeeeeeeee eeeeeeee ee eeee eeeeeeee eee eeeeeeeeee eeee eeeeeeeee ee eeeeee ee eeeee, eeeeee eeeeee eeeeeee ee eeeeeeeeeeeeee eeee eee eeeee ee eeeeeeeeeee eeeeee ee eeeeeeee eee eeeeeeeeeeee eeeee.[‌888‌] Mee eeeeeee eeeeeeeeee eeeeeeeeeeeee, eeeeeeee eeeeeeee, eee eeeeeeeeeeeeee eeee ee e eeeee eeeee ee 8:8:8.8 eee e eeeeee eeeee eeee eee eeeee eeee eeeeeeeeee eee eeeeeeeeeeee ee eeeeeeeee eeeeeeee. Meeeeee eeeeeeee ee eeee(8-eeeeeeeeeeeee eeeeeeeeeeeeeeeee) (eeeeeeeeee 88% eeeeeeee eeeeeeee) eeee eeeeeeeeeeeeee eeeeeeee eeeeeeeeeeeee (88%) eee eeeeee ee eeeeeeeeeeeeeeeeeee eeee, eee eeeeeee eeeeeeeeee eeeeeeeeeeeeee eeee eeeeee eee eeeeeeeee ee eee eeeeeeeeeee eeeeeee ee 88% eeeee eeeeeeee eeee 88% ee eee eeeeeeeeeee.

Meeee eeeeeeee ee e eeee eeee ee eeee(8-eeeeeeeeeeeee eeeeeeeeeeeeeeeee) eee eeeeee eeeeeeeee eeee eee eeeeeeee eeeeeee ee eeeeeeeeee eee eee ee eeeeeeeeeee ee eeeeeee eeee eeeee, eeeeee, eee eeeeeeeeeee eeee eeeeeeee eeeeeeee.[‌888‌]

M eeeeeee eeeeeeeeeeee ee eeeeeeeee eeeeeeee eeeeeeee eeee eeee eeeeeeeeee ee eee eeeeeeeeeeee ee eeeeeeee ee eeeeeeee ee eeeeee eeee eee eeeeeeeee ee 8888% (ee eeeeee) ee eeeeeeee eeeeeeee eee eeeeeeee (8,8,8-eeeeeeee-8,8,8-eeeeeeee).[‌888‌]

Meeeeee eeeeee eeee eee eeeee ee eeee eeeeee eeeeeeeee eeee eeeeeeeee eeeeeeee eeeeeeee. Mee eeeeeeee eeeeeeee/eeeeeeee eeeee eeeeee eeee e eeeeeeee eeeeeeee/eeeee eeeee ee 88:8 (888, e=88) eee eeee eeeeee ee eee eeeeeeeeeee ee eee eeeeeeeeeeeeeeeeeeeee eeeeeeee.[‌888‌] Mee eeeeeeeee ee eee eeeeeee (Meeeee 88) ee eeee ee ee eeeeeee ee eee eeeeeeeeeee eee eeeee.

Meeeeee eeeeeee eeee eeeeeeeeeeeeeeeeeeeee eeeeeeeee eeeee 888 (e=8) eee eeeeeeeee ee Meeee 88. Meeeeeeeeeeeee eeeeeeee eeeeeeee 888, 888, eee eeeeeeeee-8-ee (888) eeee eeee eeee eeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeee, eeeeeee 8,8-eeeeeeeeeeeeee-8,8-eeee (888) ee eeeeeee ee eeeeeeeeeeeeee eeeeeeeeeeeeee ee eeee eeeeeeeeeeeeeee eeeeeeeeee 888. Meeeeeeeeeee ee e eeeeeeeeeeee eeeeeeeeeee eeeeee eeeeeeeee ee eeeeeeeeeeeee ee eee eeeeeeee ee eee-eeeeeeeeee (888) eeee eee-eeeeeeeee-8-ee eeeeeeee (888). Meeeeeeeeeee eeeee eeee eee eeeee ee eeeeeeeeeeeeeeeee, eeee eeeee eeeeeeeee eeeeeeee eeee eee ee eeeeee eeeeeeee eeeeeeeeeee; e eeee eeeeeeeeeeee eeeee ee eeeeeeee eeee eeeeeee 888 eeee e eeeee eeeee eeeeeeee eeeeeeee/eeeeeeee eeeee ee 88:8 ee eeee.

Meeeee 88 Meeeeeeee ee Meeeeeee Meeeeeee/Meeeeeee Meeee[‌888‌]

Meeee 88 Meeeeeeee ee Meeeeeeeeeeee Meeee Meeeeeee Meeeeeee/Meeeeeee Meeee[‌888‌]

Meeeeeeee Meeeeeeeeee Meeeeee Meeee (%) Mee
ee, 8e 88 [‌888‌]
ee, 8e 88 [‌888‌]
ee e [‌888‌]
ee, 8e 88 [‌888‌]
MeMM ee, 88e MeM 88 [‌888‌]
MeMM 88°M, 88e MeM 88 [‌888‌]
MeMM ee, 8 ee MeM 88e [‌888‌]

e Meeeee eeeeeeee ee e eeeee eeeeee eeeeeee 888 (e=8) ee eeeeeeee ee eeeeeeeee ee MM8Me8 ee 88°M, eee eeee eeeeeee ee eeeeeeeeeee eeeee.

e Meee eeeeeee eeeeeeee; eeeee eee eeeeeeee.

e Meeeeee 888 (e=88) eee eeee; eeeeeeeeeeeee, eeeeeeeeeeee eeeee (8%) eee eeeeeeeeeeee (88%) eeee eeeeee.

Meeeee 88% eeeeeeee eeeeeeee/eeeeeeee, eeeeeeeeeeeee eeeeeeeeeeeeeeee ee eee eeee ee eeeeeeee eee eeeeeeeeeeeeeeeeeeeee eeeeeeee. Meeeeee, eeeeeeee ee eeeeee eeeeeeeeeeeee (ee ee eeeeeeeee eeeeee ee eeeeeeeeeeeee) ee eeeeeeee ee eeeeeeeeee eeee eeeeeeee.[‌888‌]

Meeeeeee eeeee ee eeeeeeeee ee eeeeeeee eeeeeeee eeee eeeeeee eeeee eeee eeee eeeeee eeee eeeeee, eeeeeeeeeeeeee eeeeeeeeee eeee. Meee eeeeeee eeee ee eeeeeeeee eeeeee eeee eeeeeeee eee eeeeeeeee eeeeeeee. Mee eeee ee eeeeeee ee eeeeeeeeeee ee eeee eeeeeeeeeeeeee eeeeeeeeee eeeeeeee eeee eeeeeeee eee ee eeeeeeeeeee eeee eeeee eeeeeeeee, eee eeee eee eeeeeeeeeee eeeeeee eeeeeeeee ee eeee eeeeeee eeeeee ee eeeeeeee eee eeeeee eeeee eeeeeeee eeeeeeeee.

Meeeeeeeeeee Meeeeeeee

88% Meeeeeee Meeeeeee/Meeeeeee (888):[‌888‌]

MMMMMMM: Meeeeeee eeeeeeee eeeee eee eeeeeeee eeeeeeeeee eee eeeeeeeee eeeeeeeeeee ee eee eeeeeeeeeee eeeeee.

MMMMMMM: Mee eeeeeeeeeee ee eeeeeeee ee eeeeeeee eeeeeeee ee ee eeeeeeeee eeeeeeeeee eeeeeee eeee eee ee eeeeeee ee eee eeee eeeeeeeeeee ee eee eeeeeeeee eeeeeeeeee ee -88°M.

Meeee MM (888e, 8eee) eee eeeeeeeee eeee eeeeeee-eeeee eeeeeeee (88e, 8.88eee) (eeeee eeee eeeeeeeee eeeeee) ee e eeeeeeeeeeee eeeeee ee 88°M. Mee eeeeeee eee eeeeeee ee eeee eeeeeeeee ee ee eee eee eeeeeeeee eeee eee 88% MM ee eeeeee. Mee eeeeeeeeeeeee ee eee eeee eeeee ee eeeeeeeee ee eeeeeeeeee eee eeeeee ee MM eeeee.

8-Meeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeee eeeeeeee eeeee eee eeeeeeee eeeeeeeeee eee eeeeeeeee eeeeeeeeeee ee eee eeeeeeeeeee eeeeee.

MMMMMMM: Mee eeeeeeeee eeeee eeeee eeeeeeee eeeeeeeeeeee eeeeee eeeeeeeee. Meeeeeeeeeee eeeeeeeeee eee eeeeee eeeeeeee eeee ee ee eeee.

M eeee ee e-MeMM (8.8e, 8.8eee) ee eeeeee (88eM) eee eeeee eeee 88eee ee 88% MM/eeeeeeee (888eM) ee e eeeeeeeeeeee eeeeee eee eee eeeeeee eee eeee ee ee eeee eeeeeeee eeee 8e. Mee eeeeeee eee eeee eeeeee ee 88°M, eee eee eeeeeee eeeee eee eeeeeeeee ee e eeeeeeeeeeee eeeeeeeeee eeeeee. Me eee eeee eeeeeeeee, eeeeeeeeee eee eeeeeee ee e eeee eeee eeeeee ee e eee eee/eeeeeee eeee; eeeee: 8.8e (88%); ee 8888°M.

Meeeeeee Meeeeeee/Meeeeeee Meeee eeee ee Meeeeeeeeee Meeee Meeee ee 8:8 (888, e=8); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeee eeeeeeee eeeee eee eeeeeeee eeeeeeeeee eee eeeeeeeee eeeeeeeeeee ee eee eeeeeeeeeee eeeeee.

MMMMMMM: Mee eeeeeee eeeeeee eeeeeeeee ee eeeeeeee eeeeeeeeee, ee eee eeeee 8-88 eM ee MM eeeeee ee eeeee eeee eeeeeeeee.

Me8M (ee 88.8°M; 88e, 8.88eee) eee eeeeeeeee eeee e eeeeeeeeeeee (Meeeeee eeeee) eeeeee ee 88°M eeeee eee eeeee. Meeeeeeeeeee eeeee MM (ee 88.8°M; 88e, 8.8eeee) eee eeeee ee eeeee eeeeeeee eeee eeeeeeeeee eeeeeee. Mee eeeeeee 888 eee eeeeee ee e eeeeeeeeee, eeeeeeeee eeeeee, eeeee eee eeeeee ee ee. Mee eeeeeee eee eee eeee MM eeee eeeeee ee e eeeeee Meeeeee eeeeee eee eeeee ee eeeeee ee e eeee eeee. M eeeeeeeeeeee ee eeeeeeeeeee eee eeee-eeee eeeeeee.

eee-Meeeeeeee-8-ee Meeeeeee (888):[‌888‌]

Meeeeee 888 (e=8; 88.8eM) eee eeeee eeeeeeee eeeee eeeeeeeeee eeeeeee eee eeeeeee ee e eeeeee (88 ee 88°M) eeee ee eee-eeeeeeeeee (888; 8.8e, 88eeee) ee MM8Me8 (8eM) ee e eeeeeeeeeeee eeeeee (88eM). Meeee eee eee eeeeeee eee eeeee, eee eeeeeee eee eeeeeee ee ee eeeee eeeeeeeeeeee eeeeeeeeee eee eeeeeeee ee MMM (88e). Meee, eee eeeeeeee eee eeeeeeee eeee eee-eeee M8M eee eee eeeeee eeee eeeeeeeee. Mee eeeeeee eeeee eee eeeeee eeee M8M (8×) eeeeeeee ee ee MeMMM8. Meeee eeeeeeeeeee ee eee eeeeeee, eeeeeee 888 eee eeeeeeee ee eeeeeeeeeeee; eeeee: 8.8e (88%); 88M MMM (MMMe8, δ): 88.8 (e, 8MMM=888Me), 88.8 (e, 8MMM=88Me), 88.8 (e, 8MMM=88Me), 88.8, 88.8, 88.8; 88M MMM (MMMe8, δ): 888 (e).

References


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