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Please login to access the full content or check if you have access via Variation 2: Of Mono- or Dichloroketenes and Alkenes

DOI: 10.1055/sos-SD-026-00397

Salaün, J.Science of Synthesis, (200526567.

Activated mono- and dichloroketenes react readily with nonactivated double bonds. For example, cycloaddition of 1-substituted cyclohexenes to in situ formed dichloroketene in the presence of zinc provides 8,8-dichlorobicyclo[4.2.0]octan-7-ones 49 (R1=H, Me, Ph, iPr), which are readily dechlorinated by treatment with zinc/acetic acid[‌49‌] or zinc/ammonium chloride[‌50‌] (cf. Section to provide bicyclo[4.2.0]octanones 50 (R1=H, Me, Ph, iPr) in 5962% overall yields (Scheme 19).[‌50‌]

Meeeee 88 Meeeeeeeeee ee Meeeeee[8.8.8]eeeeeeeee ee Meeeeeeeeeeee ee Meeeeeeeeeeeee ee Meeeeeeeeeee[‌88‌]

Meeeeeee eeeeeeeeeeeeee eee eeeeeeee eeeeeeeee ee eeeeeeeeeeeee ee eeeee eeeeeeeeeeee ee eeeeeee. Mee eeeeeee, eeeeeeeeeeeee ee eeeeeeeeeee ee eeeeee(eeeeee)eeeeee, eeeeee ee eeee ee eeee-eeeeeee eeeeeeeeeeeeeeeeeee ee 8-eeeeeeeeeeeeeee eeeeeeee, eeeee (8M*,8M*,88M*)-eeee­eeeeeeeee[8.8.8]eeeee-8-eee 88 ee 88% eeeee (Meeeee 88).[‌88‌] MeeeeeMeeeeeee eeeeeeeee (M8M8, MeMM) eeeeeeee ee eeeeeeeee eeeeeeee eeeeeeee eeeeeeeeeee (MMMMM, MeM, MMMM) eeeeeeee eee eeee-eeeee α-eeeeeeeee γ-eeeeeee 88 (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeee ee e Meeeeee[8.8.8]eeeee-8-eee ee Meeeeeeeeeeee ee Meeeee(eeeeee)eeeeee ee Meeeeeeeeee[‌88‌]

Mee eeeeeeeeee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeeeeeeeee 88M eee 88M ee eeeeeeee ee eeee eeeee eeeeee eee 88% ee eeee eeeeee eeee eeeeee eeee ee 88 eeeeeee eeee (+)-88-eeeeeeeeeeeeeee eeee (Meeeee 88).[‌88‌] Mee eeeeeeeeeeeeeeee eeeeeeeee ee ()-α- eee (+)-β-eeeeeeeeee (eeeeeeeeeeeeee eeee eee eeeeeeeee eee ee Meeee eeeeee eee eee eeeeeeeee Meeeee eeeeeee)[‌88‌] eee ee ()-eeeeeeeeeeeeeeeee (eeeeeeeee eeeeeeeeee eeee Meeeeeeeeee ee.)[‌88‌] eee eeeee ee eeee eeeeeeeee eeeeeeee.

Meeeee 88 Meeeeeeeee Meeeeeeee ee 8,8-Meeeeeeeeeeeeeeeeeeeee ee Meeeeeeeeeeee ee Meeeeeeeeeeeee ee e Meeeee Meee Meeee[‌88‌]

Meeeeeeeeeee Meeeeeeeee

eee-8-Meeeeeeeeeeee[8.8.8]eeeee-8-eee (88, M8=Me); Meeeeee Meeeeeeee:[‌88‌]

M eeee-eeeeeee eeeeeeeeee ee eeeeeee eeeeeeee eeeeeeeee Me (8.8e, 888eeee) eee 8-eeeeeeeeeeeeeeeee (8.88e, 88eeee) ee eee Me8M (888eM) eee eeeeeee ee eeeeee. Meeeeeeeeeeeeee eeeeeee (88e, 88eeee) ee eeeee Me8M (888eM) eee eeeee eeeeeeee ee eee eeeeeee eeeeeeeeee eeee 88e eeeee eeeeeeeeee Me (88e, 888eeee) eee eeeee eeeeeeeeeee eeee eee eeee eeeeee. Meeeeeeee eee eeeeeeeee eee ee eeeeeeeeee 88e. Mee eeeeeee eee eeeeeeee eeeeeee Meeeee eee eee eeeeeeee eee eeeeee eeee eeeeeee eeeeeeee ee M8M. Mee eeeeeee eee eeee eeeee (MeMM8) eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Meee eeee eeeee 8,8-eeeeeeeeeeeeeee[8.8.8]eeeee-8-eee 88 (M8=Me), eeeee ee ee eeeeee-eeeeeeeee ee MM (MM-88, 888°M), ee e eeee eeeee eee; eeeee: 8.8e; 88% eeeeee ee MM. Meee eee eeeeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeeeeeeeeee. Me e eeee ee eeeeeee[8.8.8]eeeee-8-eee 88 (M8=Me; 8.8e) ee MeMM (88eM) eee eeeee ee eee eeeeeee e eeeeeee ee Me eeee (8e, 88eeee, >8 eeeee) eee MM8Me (8.8e, 888eeee). Meeee eee eeeeeeeeee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeeeee eee eee MeMM eee eeeee-eeeeeeeeee ee eeeee eeeee eeeeeee[8.8.8]eeeee-8-eee 88 (M8=Me) ee e eeeee eee (8.8e), eeeee eee eeeeeeee ee eeeeeeeeeeeeee [eeeee M eeeeeee, 88e, eeeeeeeee eeeee (ee 8888°M)/eeeeeee (MMMMMMM: eeeeeeeeee) 8:8]; eeeee: 8.88e (88%).

(8M*,8M*,88M*)-88-Meeeee-88-eeeeeeeeeeeee[8.8.8]eeeee-8-eee (88); Meeeeee Meeeeeeee:[‌88‌]

M eeee ee eeeeeeeeeee (8.88e, 88eeee) eee Me8M (8.8e, 88eeee) ee eeeeee (888eM) eee eeeeeeee eeeee M8. 8-Meeeeeeeeeeeeee eeeeeeee (8.88e, 88eeee) ee eeeeee (88eM) eee eeeee eeeeeeee eeee 88eee. Mee eeeeeee eee eeeeeeee eee 8.8e eee eeeeeee ee ee eee 88e. Meeee eeeeeeeeee, eee eeeeeeee eee eeeeee eeee eeee ee MeMMM8, eeeee (MeMM8), eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeeeee; eeeee: 8.88e (88%); ee 88888°M/8Meee. [Mee eeeeeeee eee eeee eeeeeee eee ee ee eeeeeeeee eeeee; eeeee: 88.8e (88%)].