Science of Synthesis

Roy, K.-M., Science of Synthesis, (2010) 47, 1138.

The synthesis of dienes with isolated double bonds by Grignard reaction of an allylmagnesium halide with an alkene is discussed in Houben–Weyl, Vol. 5/1b, p 482. Since these uncatalyzed reactions often give low yields or form mixtures of isomeric products, more selective coupling procedures have been developed. For example, the 1,4-diene ‌8‌ is synthesized in high yield by Grignard reaction of 2-chlorocyclopentanone with allylmagnesium chloride and subsequent elimination (‌Scheme 6‌).[‌18‌]

‌Meeeee 8‌ Meeeeeeee ee 8-Meeeeeeeeeeeeeeee[‌88‌]

Mee M- eee M-eeeeeee ee 8-eeeeeeeee-8-eee (‌8‌) eeeee eeee eeeeeeeeeeeeeeeeee, eeeeeeee eeee e Meeeeeee eeeeeee eee eeeeeeeeeeee, ee eeee eeeeeeeeeeee eeeeeeeeeeeeeeeee, eeeee eee eeeeeee eeee eeeee eeeeeee eeeeeeee eee M- eee M-8,8-eeeeee ‌88‌ eeee eeeeeeee eeeeeeeee ee eeeeeeeeeeeee (‌Meeeee 8‌).[‌88‌]

‌Meeeee 8‌ Meeeeeeee ee (M)- eee (M)-Meeeeeeee-8,8-eeeeee[‌88‌]

Meeeeee 8,8-eeeeee eeee eeee eeeeeeee ee eeee eeeeee ee eeeeeeeee eeeeeee eeeee eeeeeeee ee eeeeeeeeeeeeeee eeeeeeeeeee eee(eeeeeeeeeeeeee) eeeeeeeeeeeee, eeeee eee eeeeeee eeeeeeeee eeee Meeeeeee eeeeeeee (‌Meeeee 8‌).[‌88‌] Meeeeeeee eeeeeeeee eeeee eeeeeeee(eeeee)eee eeeeeeee eeeeeee ee Meeeeeee eeeeeeee eee eeeeeeeee ee Meeeeee ‌88.8.8.8.8.8‌.

‌Meeeee 8‌ Meeeeeee ee Meeeeee Meeeeeeee Meeeeeeee eeee ee Meeeeee Meeeeeee Meeeeee[‌88‌]

Meeeeeee ee eeeeeee eeeeeeee eeeeeeeeee ‌88‌ eeee γ-eeeeeeeeeee eeeee Meeeeeee eeeeeeee ‌88‌ eeeeeeee eeeeeeeeeeeeeeee ee eee eeeeeeee ee e eeeeee eeeeeeee ee eeee eeeeeeeeeeeee eee eeeeee ‌88‌ eeeee eeee eee eeeeeee ‌88‌ eee ‌88‌ (‌Meeeee 8‌).[‌88‌]

‌Meeeee 8‌ Meeee Meeeeeee ee Meeeeee Meeeeeee Meeeeeee eeee Meeeeee Meeeeeeeee[‌88‌]

‌Meeeeeeeeee 8‌

e Mee eeeeeeee eee eeeeeeeee ee eeeeeee/Me8M (8:8) ee 8°M eee 8 e.

Meeeeeeeeeee Meeeeeeee

8,8-Meeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

Mee eeeeeee Meeeeeee eeeeeeee eeee eeeeeeee ee eeeeeee: Me eeeeeeee (8.8 e, 88 eeee) eeee eeeeee ee e 88-eM Meeeeee eeeee eeeee ee eeeee eeeeeeeeee eee eeeeeeeeee eeeeeee ee ee eee 8–8 e. Mee eeeeeeeee Me eeeeeeee eeee eeeeeee eeee eeeee MMM (8 eM) eee eeeeee ee −88°M, eee e eeee ee eee eeeeeee eeeeeeee (88 eeee) ee MMM (88 eM) eee eeeee eeeeeeee ee −88°M eeeeee 8–8 e. Meeee eeeeeeee ee 8°M eee 8–8 e, eee eeeee eeee ee ‌88‌ (8.88–8.88 M) eee eeeee ee eee.

Me e eeee ee MeMM (8.8 ee, 8.888 eeee) eee MeMe (8.8 ee, 8.888 eeee) ee eeeee MMM (8 eM) eeeee ee eeeee eeeeeeeeee eee eeeee eee eeeeeeeee ‌88‌ (8.88 eeee). Me eeee eeee eee eeeee eeeeeeee e 8.88–8.88 M eeee ee eee eeeeeeeeeeeeee eeeeeeee (‌88‌; 8.88 eeee) ee MMM ee −88°M eeeee ee eeeee eeeeeeeeee, eee eee eeeeeee eee eeeeeee ee eeee eeeeeeeeeee eee 8 e. Mee. ee MM8Me (88 eM) eee eeeee ee −88°M eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8), eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee) eeee eee eeeeeeee eeeeeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 8e, 888.
• 8.Meeeee-Meee, (8888) M 8e, 888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.