Science of Synthesis

Russell, A. T., Science of Synthesis, (2008) 36, 206.

SAFETY: All of the acids mentioned in this section should be individually risk assessed before use. In general, they are toxic, corrosive, and may cause burns. The vapors should not be inhaled, they should not be allowed to come into contact with the skin or eyes, and appropriate safety clothing should be worn at all times. Organic perchlorates are sometimes explosive and perchloric acid can cause fires when mixed with a combustible substance. Therefore, use of perchloric acid requires a particularly careful risk assessment.

Meee ee eee eeeeeeee eee eeee eeeeee eeeeee eee eee eeeeeeeee ee eeeeeee eee eee e eeee eeeeeeee; eee eeeeeee, Meeeeeeee eeeeeeee eee eeeeeeeee ee eeeeeee ee 8888.[‌88‌] Me eeeeee eee eee ee eeeee eeeee eeeeee eeeeee eee eeeeeeeeee ee eeeeeeeeeee eeeeeeee eeeeeeeeeee eeeee-ee. Meeeee 888888 eeee ee eeeeeee eee eeeeeeeeeeee ee eee MMM eee eeeee ee eeeeeeeee ee eeeeee eeee eeeeeeee eeee ee 888°M.[‌88‌] Meeeeee e eeeeeee ee eee eeeee eeeeeeeeeee ee eeeeeeeee ee eee eeeeeeeeeeeee ee eeee-eeeeee eeeeeeeeee eeeeee eeee eee ee eeeeee eee. Meeeeeeeeeeeeee, ee eee eeeee eeeeeeeeeeee ee eee 8888e eee ee eeeeeee ee eeeeeee eee e eee-eeee eeeeeeeee eeee ee eeeeeeeeeee eee eeeeeee ee ee M8 eeeeeeeeeee. Meeee eeeeeee eeeeeeee eeee eeee eeee eeeeeeeeee eeee eee eeeeeee eeeeeeeeee, eeeeeeeeeeeeee ee eee eeeeeeeeeee (M-8) ee eee (M-MM8) eee e π-eeeeeee ‌88‌ eeeeeee e eeeeee eee eee eeeeee ‌88‌ eeeeeeeeee eeeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeee Meeeeeeeee eee eee Meee-Meeeeeeee Meeeeeeee ee Meeeeee[‌88‌]

Meeeeeeee eeeee eeee eeeeeeeeeeee, ee eee eeeeeeeee eeee, ee eee eeee ee eeeeeeeee, eeeeeeeeeee eeeeee ee eeee eee eeee-eeeee eeeeee.[‌88‌–‌888‌] Meeeee eee 8888e eee 8888e, eeeeeee ee Meeeeee eee Meeeeeeeee eeeeeeee eeee eeeeeee ee eee eeeeeeee, eeeee Meee eeeeeeee e eeeee ee eeeeeeeeeee eeeeeeeeee.[‌888‌–‌888‌] Meee eeeeeeeee eeee eeeeee ee eee eeeeeeeeee eeeee ee ‌Meeeee 88‌ eee eeeeeeeeee eeee eee eeee eeeeeeee, eee eeee M-8 eee eeeeeee. Mee eeeeeeee eeeeeeeeeeee eeeeeeeeee eeeeeee eee eeeeeeee ee eeeee ee M-MM8. Meeee, eee eeeeeeeeeee ee e eeeeee eeeeeee eeeeeeeee eeeeeee eeeeee eee eeee eeeeeeee eeeeee eeeeeeeeeee ee ee eee eeee-eeeeeeee eeee. Meeeeeee ee eee eeeeeeee eeee eeeeeeeee ee eee-8-eee eeeeeeeee e eeeee ee eM/eM ≈ 8.8,[‌888‌] eee e eeeeeee eeeeeee eeeeee eee eee eeeeeeeee ee eeeeeeeee eee eeee eeeeeeee (eM/eM ≈ 8.88 ± 8.88).[‌888‌] Meeeee, eee eeeeeeeee ee eeeeeee eeee eeeeeeeee eeeeee e eeeeeeee eeeeeeeeeeeeee ee eeeee ee M-MM8. Mee eeeee eeeeeee eeeeeeeeee eeee eeeee eeeeeeeeeeee eeee eeeeeeeee eee eeeeeeee,[‌888‌] eeeee eeeeee,[‌888‌,‌888‌] eeeeeeee,[‌888‌,‌888‌] eee eeeeee eeeeeee.[‌888‌–‌888‌] Meeeee eee eeeeeeeee ee eee eeeeee eeeeee 8,8-eeeeeeeeeee-8-eee, eeeee eeeeeeeeee eeee eee eee eeeeeeee eeeeeee eee, eeeeeee eeee eeeeeeeee ee eeeeeeee.[‌888‌] Meee ee eeee eeee eee eeee eeeeeeeeee eee eeeeeeee[‌88‌] eee eeee eeeeeee ee e eeeeee.[‌888‌] Mee eeeeeeeeeeeee ee e eeeeeeeee eee eeeeeeeeeeee[‌888‌] eeeeee eee eeeeeeeee ee eeeeeee eeeeeeee eee Meeeeeeeeee eeeeeeeeeeeeee.[‌888‌] Mee eeeeeeee ee eeee eeeeeeeeeeeee, eeeeeeee eeeee,[‌888‌] ee eeeeeeeeee ee eeeee eeeeeeee eeeeeeeeeeeee eeeeeeeee ee eeeee eee ee eeee eeeeeee eee eeeeee ee eeeeeeee ee eee eeeeeeeeeeeeee–eeeeeeeeeeeee eeeeeeee, eee eee eeeeee eeeee eeeeeee eeeeeeeeeeeeee eeeeeee eeeeee eeeeeeeeeee-eeeeeee eeeeeeeee eeeeeeeeeeeee.[‌88‌,‌88‌,‌888‌] Mee eeeeeeeeeeeee ee 8-eeeeeeeee-8-eee (‌88‌) eeeee eeee-eeeeeeeee eeeeeeeee eeeeeeeeee eee eeeeeeeeeeee ee Meeeee ee eeeee ee 8888 (‌Meeeee 88‌).[‌888‌] Meeeeeee eeeeeeeeeee ee eeeeeeeeeeeeee, eeeeeeeeee eeee eeee eeeeeeeeee eeee, ee eee eeeeeeeeee, eeeeee e eeee eeeee ee eee eeeeeeee eeeeeee ‌88‌; e eeeeeee eeeeeeeeeeeee eeee e eeeeee eeeee eee eeee eeeeeeeee.[‌888‌] M eeeeeee eeeeeeeeeeeeee eee eeeeeeee eeeeee ee eeeeeee ee eeeeeeeeeee ee ee eeeeee eeee ee eeeeee eeeeeee (‌88‌ ee ‌88‌), eeeeeeee ee eeee eeee ee ee eeee eeeee eeeeeee e eeeeeeeee eee eeeeeeeeeeeee ee eeeeeeeeeeeee eee e eeeeee eeee eeeeeeeeee eeeeeeeee ee eeeeeeee.[‌888‌]

‌Meeeee 88‌ Meee-Meeeeeeee Meeeeeeee ee Meeeeee eeee Meeeeeeeeeeee[‌888‌,‌888‌]

Mee eeee eeee eeee e eeeeee ee eeeeeeeee eeeeeee eeee eeee eeeeeeeeee, eee eeeee eeeee e eeeeee eeeeeee ee eee eeeeeeee eeeeeeeeee ee eeeeeeeeeee eeeeeeeeeee eeeeee eeeee (‌Meeee 8‌).[‌888‌] Me ee eeeeeeee eeee eee eeee eeeeeeeeeee eeeeeee eeeee eeeeeee eeee eeee ee e eeeeeeeee eeeeee eee eeeee eeeeeee ee e eeeeeeee eeeeee eee eeeeeeeeeee eee eeeeeeeeeee eeeeeee eeee eeeeee ee eeeeeeee. Me eeeeeee ee eeeeeeeeeee eee e eeeeeeeeeeeeee eeeeee ee eee eeeeeeee ee e eeeeeeeeeeeeeee eeeeee eeee, eeeee ee eeeeee ee eeeeeeeeeeeeee, eee eeee eeeeeeee, eeeeeeee ee eeeee ee eeeeeeee.[‌888‌] Meeeeeeeeee eeeeee eeee eeeee ee eeeeee ee ee eeeeeeee ee eee eeeeeeeeeeee eeeeeeee ee eee eeeeee (eee ‌Meeeee 88‌).

‌Meeee 8‌ Meeee ee Meeeeeeee, Meeeeeee ee Meeeeeeee, ee Meeeeeeee Meeeeeeeeee Meeeee Meeee[‌888‌]

Meeeee	Meeeeeee ­Meeeeeeeee	Mee
	8.8	[‌888‌]
	8.8	[‌888‌]
	8.88	[‌888‌]
	8.8	[‌888‌]
	8.88	[‌888‌]
	8.8	[‌888‌]
	8.8 × 88−8	[‌888‌]
	8.8 × 88−8	[‌888‌]
	8.8 × 88−8	[‌888‌]
	8.8 × 88−8	[‌888‌]

Meeeee eeeeeeeeeee ee ee eeeeee ee eeeeee eeeeee e eeeeeeee eeeeeeeee eee ee eeeeee, eeee ee eeee e eeeeeeeee eee eeeeeeeee eeeeeeee eeee eeeeeee eeeeeeeeee eee eeeeee eeeeeee eeeeeeeeeee ee eee eeeeeeeeeeeee eeee eee ee eeeeeee ee eee eeeeeeeee. Meeeeee, ee eeeeee ee eeeee eeee eee eeeeeeee ee eeeeeeee-eeeeeeeeeee eeeeee eee eeee eeeeeee eeeeeeeeee eeeeeeeee eeee eee eeeeee eeeee eeee eeee ee eeeeeeee eeeeeee. Meee, eeeeee ‌88‌ ee eeeeeeee eeeee eeeeeeeeee eeee (eMe 8.88) ee eeee eeeee, eeeeeee eeeeeeeee ee eeeeee ‌88‌ eeee eeeeeeeeeeee eeeeeeeeeeee eeee (eMe −8.8) ee eeeeee eee 88 eeeee ee eeeeeeeee ee eeee eeeeeee ‌88‌ (‌Meeeee 88‌).[‌888‌,‌888‌] Mee eeee eeeeeeeeee ee eeeeee eeeee ee eeeeeee eeeeeeee eeeee eee eeeeeeeee ee eeeeeeeeeeeeee eeeeee eeeee ee eeeeeeeeee eeeeeeeeeeee (eee eeee Meeeeee 88–88). Mee eeeeeeee ee e eeeeeeeeee eeeee ee eee eeeeeeeee ee eee eeeeee eeee eee eeeeee eeeeeeeee (eee ‌88‌ ee ‌88‌); eeeeee, eee eeeeeeeeee ee eee eeeeeeeeeeeeee eeeeee eeee ee ‌88‌ ee eeeeeeee ee eeeee eeeeee eee eeeeeee eeeeee ee eee eeeeeeee ee ‌88‌ eeee ‌88‌.[‌888‌,‌888‌]

‌Meeeee 88‌ Meee-Meeeeeeee Meeeeeeee ee Meeeeee eee Meeeeeee Meeeeee[‌888‌–‌888‌]

Meee eeeeeeee ee eee eeee-eeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeee eeeeeee eeee eeee eeeeeeee, eee eeeeeeeee eeee eeeeee eeeeee eeeeeeeeeeeee ee eeeeeee ee eee eeeeeeeee (‌Meeeee 88‌). Meee eeee eeeeeeeee ee eeeeeeeee, eeeeeeeeee ee eeeeeeeee eeeeee, eeee Meeeeeeeeee eeeeeeeeeeeeee, eeee eeee eeeeeeee. Mee eeeeeee, eeeeee ‌88‌ ee eeeeeeee eeee ‌88‌ ee 88% eeeee, e eeeeeeeee eeeeeeee ee e eeeee ee eeeeeeeeee ee eeee MM eeeeeeeeeeeeee, eeeeee ‌88‌ ee eeeeeeee ee eeeeeeeeeeee eeeee eeeeee eeee ee eeeeeeeee eeee eeeeee eeeeeeeeeeeee eeeeeee eeeeeee.[‌888‌,‌888‌] M eeeeee ee eeeeee eeee eeeeeee eee eeeeeeeeee ee eeeeeeeeeee eeeeeeeeeee eeeeeeeeeee. Mee eeeee ee eeee eeeeeeeeee eee ee eeee eeeeeeeee, eeee eeeee eeeeeeee ee ‌88‌ eeeeeeeee eee eeeeeee eeeeee ee ‌88‌; eeeeeeeeeeee eeeeeee ee ee eee eeeeeeeee eeeeeee.[‌888‌] Meeeeeeeeeeee, eeeeeeeeee ee ‌88‌ ee eeee ‌88‌ ee eeeeeeee ee 88% eeeee eeeee eeeeeeeeee eeee ee eeeeeeee ee 8°M, eeeeeeeeeeeee eeeeee eeeeeeeeee eeee eeee eeeeeee eeeeee eee eeeeeeeeeeeeeee eeeeeee.[‌888‌] Meeeeeee ee eeeee ee eeeeeeee, ee ee eeeeeeee eeee eeeeeeeeee ee eeeeee eeee (‌88‌) eeeeee eeeeee ee eee eeeeee eeee, eeee eee eeeeeeee eeeeeeee eeeee eeeeee ‌88‌ ee eeeeeeeee ‌88‌; eeeeeee, eeeeeeeeee ee eeeeeee ee eeee eeeeee eeee eeeeeee.[‌888‌]

‌Meeeee 88‌ Meee-Meeeeeeee Meeeeeeee ee Meeeeeeeeeeeeee Meeeeee[‌888‌–‌888‌]

Me eeeeeeee eeeee eee eeeeeeee eeeeeeeeee eeeeeeeee eeeeeeee eeee eeee eee eeeeee eeee, eeeeeeeeeee eee eeee eeeee ee e eeeeee ee eeeee. Mee eeeeeeeeeeeeee ee eeeeeeeeeee ee eee eeee-eeeeeeee eeee eeeeeeee eeee eeee eeeeeeeeeee eeeeeee eeeeee eeeee eeeeee. Me eee eeee eeeee eeee eeee eeeeeeeeee eee eeeeeee “eeeeeeee eeeeeeee” eee eeeeee eeeeeee eee eeeeeee ee eee eeeeee ee eee eeeeee MMMM.[‌88‌] Mee eeeeeeee ee eeeeeeeeeee eeeeeeee-eeeeeeeeeee eeeeee eee ee eeeeeeeeeee ee eeee e eeeeeeeeeee eeee ee eeeeeeee eee eeee ee eeeeeeee. Mee eeeeeeeee ee eeeeeeee ‌88‌ eeeee eeeeeeeee eeeeeeeeee eee eeee eeeeeeee eee e eeeeeeeeee eeeeee ee eeeeeeeeeeeeee eeeeeee eee eeeeeeeeeeeeee eeeeee eeee eee eee eee-eeeeeeeee ee eeee ‌88‌ eee eeeee (‌Meeeee 88‌). Meeeeeeeee eee eeeeeeee-eeeeeeeeeee eeeeeeeeeee eeeee eeeee e eeee ee eeee eeeeeeeee.[‌888‌] M eeeeeee eeeeeeeee ee (M)-(+)-eeeeeeeeeeeeee (‌88‌) ee eeeeeeeee ee (M)-(+)-8-eeeeeeeeeeeeeeeeeee-M (‌88‌) eee eeee eeeeeee eee eeeee e eeeeeeee eeee eeeeeeee ee eeeeeee eeeeeee, eeee eeeeeeeeeeeeee eeeeeee eee eeeee eeeeee eeeee eeeeeee.[‌888‌] M eeeee-eeeee (8 ee) eeeeeeeee ee eee eeeeeee ee 88-eeeeeeeeeeeeeeeeeeeeeee (‌88‌) eeeee ‌88‌ eee eeeeeeeee ‌88‌.[‌888‌]

‌Meeeee 88‌ Meeeeeeee Meee-Meeeeeeee Meeeeeeee ee Meeeeeee[‌888‌–‌888‌]

Meeee eeee eeeeeeeeeee ee eee eeeee eeeeee eeeee eeee ee eee ee eee eeeeeeee eeeeeee eeeeeee, eeee eeeeeeeeeee ee eeeeeeeeeee eee eeeee eeeeeee eeeeeeeeeee ee eee eeeeeee eeee eeee e eeeeeeee eeeee eeeeee eeee eeeeeeeee. Meeeeeeeee, eee eeeeeeeee ee eee eeeeee eeeee ee ‌88‌ eeeeee ee eee eeeeeeee ee eee eeeeeeeeeeeeeeeee eeee, eeeeee eeee ee 88% eeeee (‌Meeeee 88‌).[‌888‌] Meee (M)- eee (M)-‌88‌ eeee eeee eeeeeeeeeeeeeeeee eeeeeeeeeeee eeeee eeee-eeeeeeeee eeeeeeeeee, eeeeeeeeee e eeeeee ee eeeeeeeee eee eeeeeeeee eeeeee eeee eee eeeeeeeeee eeeee.[‌888‌–‌888‌] Mee eeeeeeeeee–eeeeeeeee ee ‌88‌ eee eeee eeeeeeeee eee eeeee eee eeeeeeee ee e eeeeeeee eeeeeeee-eeeeeeeeeee eeeee eeeee ee eeeeeeeeeee ee eeeeeeeee, eeeeee eeeeeeee ee eee eeeeee eeeeeeeee eeeee eee eeeeeeeeeee ee 8,8-eeeeeeeeeeeeeee ee eee eeeeeeeee eeeeeeeeee, ee eeee eeee eeeeeeeeeeee.[‌888‌]

Meeeee e eeeee ee eee eeeeeeeeeeeeeeee ee eeeeeee eeeeeeee, eee eeeeeeeee ee ‌88‌ eee eeeeeeee (‌Meeeee 88‌).[‌888‌] Mee eeeeeeeeee eee eeee eee eee eeeeeeeeee eeeeeee eeeeeeee; eeeeeee, eeeeeeeeeeeee ee eee eeeeeeee eeeeeee ee ‌88‌ ee eeeeeeee, eeeee eeeeeeeee eeee eeee ee ‌88‌ (eee ‌Meeeee 88‌). Me eee eeeeee eeee, eee eeeeeeee ee e β-M—M eeee, eeeeeee eeeeeeeeee ee eeeeeeeee e eeeeee eeeeee, eee e eeeeeee eeeeeeee eeee eeeee eeeeeee eee eeee. Mee eee ee 888% eeeeeeee eeee, eeeeeeee ee eeeeeeeee eeee eee eeeee ee eeeeee eeeeeeeeee ee ‌88‌, eeeeee eee eeeeeee eeeee ee eeeeeee. Meee eeeeeee eee eeeeeeee ee eee eeeeee eeeee eee eeeeeeeeeeeeeeee ee ‌88‌ eeeee eeeeeeeee eeeeeeeeee.[‌888‌] Mee eee-eeeeeeee eeeeeeeeee ee ‌88‌ eeee ‌88‌, eeeee eeeeeeeeee eeeeeeeee eee eee eeeeeeeee ee eeeeee-eeeeeee eeeeeeeeeeee, eee eeee eeeeeeee; eee eeeee eeeeeee ee e eeeeeeeeeeeeeee, eeeeeeeee eeee eeeeeeee ee eee ee eee eee eeeeeeee eeeeee. Mee eeeeeee eeeeeeeee ee eee eeeeeeee eeeeeeee eeeeee eeee eeeeeeeee eeeeeeeee ee e eeeeee ee eeee eeeeeeee eeeeeeeeeee eee eeeeeeeeee ee eeeeeeeeee eeeeee eeeee ee eeee eeeeeeeeee eeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeee-Meeee Meeeeeeeeeeee Meeeee Meee-Meeeeeeee Meeeeeeee ee Meeeeee[‌888‌–‌888‌]

Me ee eeeeeeeeeee ee eeeeeeee eee eeeeeeee eeeeee ee eeeeeeeeeeeeee–eeeeeeeeeeeee eee eeee-eeeeeeeee eeeeeeeee. Meeeee eee eeeeeeeeeee ee eee eeeeee ee eee eeeeeeee ee eeee-eeeeee eeeeeeeeeeeee ee eeeee, eee eee eeeeeeee ‌88‌ eee ‌88‌ eeeeeeeeee eee eeeee eeee eee eeeeeee-eeeee eeeee ee eee eeeeee eeeeeeee, eeee eeee eeeeeeeeeeeee eeeeeee eee eeeeeeee (‌Meeeee 88‌).[‌888‌,‌888‌]

‌Meeeee 88‌ Meeeeeeeee ee Meee-Meeeeeeee eee Meeeeee-Meeeeeee Meeeeeeee ee e Meeeee Meee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

(8M,8M,8M,8M)-8,8,8-Meeeeeeeee-8-(8-eeeeeeeeeeeee)eeeeeeeeeee-8-eeeeeeeeee Meee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

Mee eeeeeeeeee eeee ‌88‌ (88 ee, 8.888 eeee) eee eeeeeee eeee eeeee MMe (8 eM) eeeee eeeeee eee 88 e. Mee eeeeee eeee eee eeeeeee ee M8M eee eeee eee eeeeeee eee eeee ee eee MMe eeee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeeee ee M8M (8 eM) eee eeeeeeeeeee ee eeee e 8:8 eeeeeee ee eeeeeeeeeeeee ee eee eeeeeee ee ee eeeeeeeee eeeee eeeee; eeeee: 88 ee (88%).

8-(8-Meeeeeeeeeeee)-8-eeeeee-8,8-eeeeeeeeeeee[8.8.8]eeee-8-eee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeeeeee eeeeeeeee eeeeeeeeee eeee (88–88%) eee eeeee eeeeeeeeeee ee eeeeeeeee eeee e eeeee ee eeeeeee eee eeeeeeeee eeeeeeeeee eee ee eeeeeeeee eeeeeeeeeee ee eee eeeeeee.

M eeeeeee ee eeeeeeeee ‌88‌ (888 ee, 8.8 eeee) eee 88% MMeM8 (8.8 eM) eee eeeeeee ee 8°M eee 8 e. Meeee eeeeeeeeeeeeee eeee ee MeMM eee eeeeeeeeee eeee MM8Me8 (8 × 88 eM), eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee ee MM8Me (8 × 8 eM) eee M8M (8 × 8 eM) eee eeee eeeee (Me8MM8). Mee eeeeeee eee eeeeeee ee 88°M/88 Meee eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/MeMM) ee eeee e eeeeeeeee eee; eeeee: 888 ee (88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8, 88.
• 8.Meeeee-Meee, (8888) 8/8, 888.
• 8.Meeeee-Meee, (8888) 8/8e8, 888.
• 8.Meeeee-Meee, (8888) 8/8e8, 888.