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47.1.4.5.2 Variation 2: Pyrolysis of Esters

DOI: 10.1055/sos-SD-047-00322

Kostikov, R. R.; Khlebnikov, A. F.; Sokolov, V. V.Science of Synthesis, (201047813.

The pyrolysis of esters is an excellent method for alkene synthesis because of the ready accessibility of esters (especially acetates), the ease of carrying out the pyrolysis, the high yield and purity of the products, and the lack of rearrangements. On the basis of the stereochemical outcome of the reaction, a concerted syn elimination with a six-electron aromatic transition state has been suggested (Scheme 26) (see also HoubenWeyl, Vol. 5/1b, pp 105130).[‌153‌]

Meeeee 88 Meeeeeeee ee Meeee Meeeee Me Meee Meeeeee[‌888‌]

Meeeeeeeeeeeee, eeee eeeeeeeee eee eeeeeee eee ee eee eee eeeee (888888°M) ee ee eee eeeeee eeeee ee eeeeeeeeeeee ee eeee-eeeeeee eeeeee. Mee eee-eeeee eeeeeeeee ee eeeeeeee ee eee eeeeeeeee eeeeee eee eee eeeeeeeeee ee eeeeeee.[‌888‌,‌888‌]

Meeeeee ee eeeeeeee ee eeeeeee eeeeeeee, eee eeeeeeeee ee eeeee eee eeee eeeeee eee eee eeeeeeeeeee ee eeee eee-8-eeee. Meeeeee eeeeeeeee ee eeee- (e.e., 88) eee 8,8-eeeeeeeeeeeee eeeeeee eeee eeeee eeeeeeee eee eeeeeeee ee Meeee 88.[‌88‌,‌888‌,‌888‌‌888‌] Meeeeee eeeeeeeee eee eeee eeee eeee eee eee eeeeeeeee ee eeeeeee eeeeeeeeee e eeeeeeeeeee eeeeee eeeeeeee ee eee eeeeee eeee.[‌888‌,‌888‌]

Meeee 88 Meeeeeeee Meee- eee 8,8-Meeeeeeeeeeee Meeeeee ee Meeeeeeee ee Meeee Meeeeeee[‌88‌,‌888‌,‌888‌‌888‌]

Meeeeeee Meeeeeee Meee (°M) Meeeeee(e) Meeeee (%) Mee
888 88 [‌888‌]
888 88 [‌888‌]
888888 88 [‌888‌]
888 88 [‌888‌]
888 e.e.e [‌888‌]
888 88 + 8 [‌888‌]
888 88 [‌888‌]
888888 e.e.e [‌888‌]
888 88e [‌888‌]
888 e.e.e [‌888‌]
888 888 [‌888‌]
888888 888 [‌888‌]
888 88 [‌888‌,‌888‌]
888888 e.e. [‌888‌]
888 88 [‌888‌]
888 e.e.e [‌88‌]
888 e.e. [‌888‌]
888 88 [‌888‌]
888 e.e.e [‌88‌]
888 e.e.e [‌88‌]
888 e.e.e [‌88‌]

e e.e.=eee eeeeeeee.

e 888% eeee.

e >88% eeee.

e >88% eeee.

Meeeeeee eeeeeeee ee eeeeeeeee eee eeeeeeee eeeeeeee eeeee ee eeeeeeee ee eeee eeeeeeee ee eeeeeeee, eeee eeeeeee eeeeeeeee eeee eeeeeeeeee eeeeeeeeeeeeeeee, eeeeeee ee eeee eeeeeee eeeeeeeee ee eee Meeeeee eeee.[‌888‌]

Meeeeeee ee eeeeeeeee eeeeeeee ee eeee 88 eeeeeee eeeeeeeee ee 888°M ee eeee eeeeeeee ee eeeee- eee eeeeeeeeeeeee, eeeeeeeeee eee eeeeee eeee ee eee 8- ee 8-eeeeeeee (88 eee 88, eeeeeeeeeeee). Mee eeeee ee eeeee- eee eeeeeeeeeeeee eeeeeee ee eee eeeeee eeee ee eee M8 eeeee, e.e. ee eee eeeeee M8=Me, Me, eMe, e-Me eee eeeeee eeeeeeee eee eeee eeeeeeeeeeeee ee 88, eeeeeeeeee eee (M)-88, eeeeeee eeee eee (M)-88 eeeeeeeee (Meeee 88).[‌888‌]

Meeee 88 8,8-Meeeeeeeeeeee Meeeeee ee Meeeeeeee ee Meeeeeee ee Meeeeeeee Meeeeeee[‌888‌]

M8 Meeee (%) Mee
(M)-88 (M)-88 (M)-88 (M)-88
Me 88 88 8 8 [‌888‌]
Me 88 88 88 88 [‌888‌]
eMe 88 88 88 8 [‌888‌]
e-Me 88 8 88 8 [‌888‌]

Meeeeee eeee ee (M)-8,8,8,8-eeeeeeeeeeeeeee-8-eee (88) eee eeeeeeee ee eee eeeeeeeee ee eeeeee ee eee eeeeee eeeee (Meeee 88).[‌888‌,‌888‌‌888‌] Meee eeeeee eee eeeeeee eeeeeee eeee eeee-eeeeeee ee eeeeeeeee eeeeeeee eeeee eeee ee eeeeeee, eeeeeeee, eeeeeee, eeeeeeee, ee eeeeeeeeeeeeee eeeee ee eee Meeeeee eeeeee (eee Meeeeee 88.8.8.8.8) ee eeeee eeeeeeeeee.

Meeee 88 Meeeeee ee Meeeeeeee ee Meeeee ee eee Meeeee Meeee ee 888888°M[‌888‌,‌888‌‌888‌]

Meeeeeee Meeeeeee Meeeeee Meeeee (%) Mee
88 [‌888‌]
e.e. [‌888‌]
88e [‌888‌]
e.e. [‌888‌]
e.e. [‌888‌]
88e [‌888‌]
e.e. [‌888‌]
88e [‌888‌]
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]

e e.e.=eeeee eee eeeeeeee.

e Meeee eeee eee eeeee, e.e. eeeeeeeeeeeeee ee eeeeeeee eeeeeee eeee eeee eeeeeeee eee eeee eeeeeeeee.

Meeeeeeeeeee Meeeeeeee

(M)-8-Meeeeeeeee-8-eee (88); Meeeeee Meeeeeeee:[‌888‌]

(M)-8-Meeeeeeeeeee-8-ee eeeeeee (8.8e, 88.8eeee) eee eeeeeeeee ee 888888°M ee eeeeeeeeee ee eeee e eeeeee ee eeee-eeeeee M8 (8eM·eee-8) eeeeeee e eeeee eeee (888 × 8.8ee) eeeee eee eeeeee (eeee eee eeeeee ee eee eee) eeee 8-ee, 8.88-ee, 8-ee, eee 8-ee eeeee eeeeeee. Mee MeMM eeeeee eee eeeeeeeeeee eeee eeeee Me8MM8, eee eee eeeeee eee eeeeeeeee ee e eeee (888°M) eeee; eeeee eeeee: 8.8e (88%). Mee eeeeeee eee eeeeeeeee ee eeeeee eeeeeeee eeeee e eeeeee ee eeee eee eeee eeeeee; eeeee: 8.8e (88%); ee 8888°M/888Meee; [α]M88 +8.88; 88M MMM (MMMe8, δ): 888.8, 888.8, 88.8, 88.8, 88.8, 88.8.

(M)-8,8,8,8-Meeeeeeeeeeeeee-8-eee (88); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee 8,8,8,8-eeeeeeeeeeeeeeeee-8-ee eeeeeeee (88.8e, 88eeee) eee eeeee eeeeeeee (8.8eM) eee eeeeee ee ee eee eeee ee 888°M ee e eeeeeeeeeeee eeeeeeeee eeeeeeee eeee e Meeeeee eeeeee. M eeeeee eeeeee (ee 888888°M) eeeeeeeee eeee, eee eee eeeeeeeeee eee eeeeeeeee ee Me8M. Mee eeee eee eeeeee ee eeeeeee eM eee eeeeeeeeeeee ee eeeeeeeeeee ee eee eeeeeee ee eeee eee eeeee eeeeeee (8.8e; 88% eeeeee ee MM). Meeeeeeeeeee (8888°M/88Meee, eeee 88°M/888Meee) eeee eeeee eeeeeee; eeeee: 8.8e (88%; 88% eeeeee ee MM); 8M MMM (MMMe8, 888MMe, δ): 8.88 (e, 8M, MM8), 8.88 (e, 8M, MM8), 8.88 (e, M=8.8Me, 8M, MM8), 8.88 (ee, M=88.8, 8.8Me, 8M, M8), 8.88 (e, M=88.8Me, 8M, M8).

References