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31.13.1.5 Method 5: Reaction of Grignard Reagents with Sulfur

DOI: 10.1055/sos-SD-031-00879

Rakitin, O. A.Science of Synthesis, (200731952.

Aryl halides 8 containing various functional groups can be converted into the corresponding Grignard reagents, which react with a source of electrophilic sulfur (Scheme 6).[‌26‌] Elemental sulfur is suitable for this purpose, and this reaction, followed by reductive workup, has been effectively used for the preparation of various arenethiols 9 (Scheme 6).[‌27‌‌34‌] Yields range from moderate to very high, sometimes quantitative, for example in the preparation of 4-phenoxybenzenethiol (9, R1=R2=R4=R5=H; R3=OPh).[‌27‌]

Meeeee 8 Meeeeeeee ee Meeeeeeeeee eeee Meee Meeeeee eee Meeeeeee Meeeeeee[‌88‌‌88‌]

Meeeeeeeeee 8

M8 M8 M8 M8 M8 Meeeeeeeee Meeee (%) Mee
M M MMe M M 8. Me; 8. M8; 8. MeMeM8 888 [‌88‌]
M MMe8 M M M 8. Me; 8. M8 88 [‌88‌]
eMe M M MMe M 8. Me; 8. M8 88 [‌88‌]
Me Me Me Me Me 8. Me; 8. M8 88 [‌88‌]
M MM8 M M M 8. Me; 8. M8; 8. Me, MMe 88 [‌88‌]
M MMe MMe M M 8. Me; 8. M8 88 [‌88‌]
M M M M M 8. Me; 8. M8 88 [‌88‌]
M M M M M 8. Me; 8. M8 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeeeeee (8, M8=M8=M8=M8=M; M8=MMe); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeee eeeeeee eeeeeeee eeeeeee eeeeee eeeeeeeeee eeee e eeeeeee ee eeeeeeeeee, eee eee eeeeee ee eeeeeee ee eeeeeeee eeeeeeee.

Me (888ee, 88.8eeee) eee M8 (88ee, 8.888eeee) eeee eeeee ee e eeee ee eeeeeee 8 (M8=M8=M8=M8=M; M8=MMe; 8.88e, 8.8eeee) ee MMM (88eM), eee eee eeeeeee eee eeeeeeee eee 88eee, eeee eeeeeee ee eeee ee ee, eee eeeeeee eee 8e. Mee eeeeeeeee eeee eeee eee eeeeeee eeee M8 (8.888e, 88.8eeee) eee eee eeeeeee eee eeeeeee eee eeeeeee 8e. Mee eeeeee eeeeeee (8°M) eee eeeeeee eeee eeeeee MeMeM8 (8.8e, 88eeee), eeeeeee eee 88eee, eeeeeeee eeee MeMMe (8.8eM), eee eeeeeeeeeee eeeeeee MM8Me8 (88eM) eee eee. ee eeeeee eeeeeeeee eeeeeeee (888eM). Mee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (8×88eM), eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee M8M (8×888eM) eee eeeee (MeMM8), eee eee eeeeeee eee eeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 88:8); eeee eeeeeeee eeee 8 (M8=M8=M8=M8=M; M8=MMe) ee e eeeee; eeeee: 8.88e (888%).

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