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24.2.3.1.6 Method 6: Miscellaneous Eliminations

DOI: 10.1055/sos-SD-024-00188

Khlebnikov, A. F.; Kostikov, R. R.Science of Synthesis, (200624185.

Upon treatment with lithium diisopropylamide and dimethyl disulfide, 1-fluoro-1-tosylalkanes give 1-fluoro-2-(methylsulfanyl)-1-tosylalkane intermediates, which are converted into the corresponding 1-fluoro-1-tosylalk-1-enes 51 almost exclusively upon treatment with 3-chloroperoxybenzoic acid, followed by heating under reflux in toluene (Scheme 40).[‌62‌]

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M8 Meee Meeee (M/M) Meeee (%) Mee
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Me 88e 88:8 88 [‌88‌]
eMe eeeeeeeee 88:8 88 [‌88‌]
e-Me 8e 88:8 88 [‌88‌]
Me eeeeeeeee >88:<8 88 [‌88‌]
MMe 8e 888:8 88 [‌88‌]
MMMM eeeeeeeee 888:8 88 [‌88‌]

Meeeeeeeeeeee ee eeeeeee eeeeee(eeeeeeeeeeeeee)eeeeeeeeeeeeeeeee eeee eeeeeeeeeeee ee eeeeeeeeeeeeeee ee 88°M, eee eeeeeeeeee eeeeeeeee ee eee eeeeeeeee eeee eeeeeeeeeeeeeee eeeeeeeee, eeeee eee eeeeeeeeeeeeeeeeeee eeeeeeeeeee ee eeeee, eeeeeee eeeeeeeee, ee eeeee e Meeeeeee eeeeeee. Meeeeeeeeee ee eeeeeeeeee eeee eeeee eeeeeee e 8-eeee- ee 8-eeeeeee-eeeeeeeeeee (M)-8,8,8,8-eeeeeeeeeee-8-(eeeeeeeeeeeeee)eeee-8-eee 88 eeeeeeeeeee ee 8888% eeeee (eeee eeeee eeeee) (Meeeee 88).[‌88‌]

Meeeee 88 8-Meee- ee 8-Meeeeee-Meeeeeeeeee (M)-8,8,8,8-Meeeeeeeeee-8-(eeeeeeeeeeeeee)eeee-8-eee[‌88‌]

Meeeeeeeeee 88

Me8 Meeee (%) Mee
8-MM8M8 88 [‌88‌]
8-MeM8M8 88 [‌88‌]
8-Mee 88 [‌88‌]
8-Mee 88 [‌88‌]
8-Mee 88 [‌88‌]
8-MeMM8M8 88 [‌88‌]
Me 88 [‌88‌]
8-eeeeeee 88 [‌88‌]

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Meeeee 88 8-Meeeee-8-(eeeeeeeeeeeeee)eeeeeee[‌88‌]

Meeeeeeee eeeeeeeeeee ee eeeeeeeeeee α-eeee eeeeeeeeee eeee eeeeeeee(MM) eeeeeeeeeeee ee eeeeeee eeeee eeeee eee eeeeeeeeeeeee 8-eeeeee-8-(eeeeeeeeeeeeee)eee-8-eeee 88 ee eeee eeeeee (Meeeee 88).[‌88‌]

Meeeee 88 8-Meeeee-8-(eeeeeeeeeeeeee)eee-8-eeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) Mee
M 8-MeMM8M8 88 [‌88‌]
M (MM8)8Me 88 [‌88‌]
M (MM8)88Me 88 [‌88‌]
M 8-Me-8-MeMM8M8 88 [‌88‌]
(MM8)8 88 [‌88‌]

M eeeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeee eeeeeeee ee eeee ee eeeeeee [8-eeeee-8-(eeeeeeeeeeeeee)-8-eeeeeeeeee-8-eeeeeeeee]eeeeeeeeeeeee (88) (Meeeee 88).[‌88‌]

Meeeee 88 [8-Meeee-8-(eeeeeeeeeeeeee)-8-eeeeeeeeee-8-eeeeeeeee]eeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeee-8-eeeeeeee-8-eee (88, M8=Me); Meeeeee Meeeeeeee:[‌88‌]

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8-Meee- ee 8-Meeeeee-Meeeeeeeeee (M)-8,8,8,8-Meeeeeeeeee-8-(eeeeeeeeeeeeee)eeee-8-eeee 88; Meeeeee Meeeeeeee:[‌88‌]

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References


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