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DOI: 10.1055/sos-SD-212-00164

Belderrain, T. R.; Nicasio, M. C.Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (20141263.

The decomposition of diazomethane in the presence of catalytic amounts of a transition-metal complex generates a metal carbene species that can react with alkenes, affording cyclopropane derivatives (Scheme 5);[‌36‌‌38‌] see also Science of Synthesis, Vol. 48 [Alkanes (Section].

Meeeee 8 Meeeeeeeee-Meeee-Meeeeeeee Meeeee Meeeeeeeeeeeeeee eeee Meeeeeeeeeee[‌88‌‌88‌]

Meeee e eeeeeee ee eeeee eeeeeeeee eeeee ee eeeeee eeee eeeeeeeeeeeeeee, eeeeeeeee(MM) eeeeeeeee eee eee eeee eeeeeeeee eeeeeeeee.[‌88‌] Meeeeeeee eeeeeeeee eee eeee eeeeeeeee ee eee eeeeee ee eeeeeeeeeeee ee eee eeeeee,[‌88‌,‌88‌] eeeeeeeeee eeee eee eeeeeeeeeeee ee eee eeeeee ee eee eeeeee eeeeeeeee eeeeeee eeeee ee eeeeeeeee eeee ee eee eeeeeeeeeeeeeeee eeeeeeeee.[‌88‌,‌88‌‌88‌] Meeeeeee eeeeeee eee α,β-eeeeeeeeeee eeeeeeee eeeeeeeee eee eeeeeeeeeeee eeeeeeeeeeeeeee eeee eeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee(MM) eeeeeee, eeeee ee eeeeeee eee eeeeeeee ee eeeeee (Meeee 8),[‌88‌‌88‌] eeeeeee eeeeee eeeeeeee ee eeeeeeeeeee eeeeeee eeeeeee eee eeeeee ee eeeeeeeeeeeee. Meee eeeeee ee eeeeee eeeeeee eeeeeeeee eee eeeeeeeeee ee eee eeeeee eeee eeeeee eee eeeeeeee eeee eeeeeeeeeeee eeeee eeeeeeeee eeeeeeeee.[‌88‌,‌88‌] Meeeeeeeee eee eeeeeee eeeeeeee eeeeeeeeee eeeeeee eeeeee eeee eeeeee ee eeeeeeeeeeee eeeeeeeeeee ee eee eeeeeeee eeee eeeeeeeeeeee.[‌88‌,‌88‌] Meeeeeee, eeeeeeeeeeeeeeee ee eeeeeeeeee eeeeeeee ee e eeeeee eeeeeeeee eeeeee, e.e. eee-eeeeee 88 ee eeeeee eeeeeeeeeee (Meeeee 8).[‌88‌]

Meeee 8 Meeeeeeeeeeeeeee ee Meeeeeeeee eee Meeeeeeee Meeeeee eeee Meeeeeeeeeee Meeeeeeee ee Meeeeeeee(MM) Meeeeee[‌88‌‌88‌]

Meeee Meeeeeeee Meeeeee Meeee (%) Mee
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Meeeee 8 Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeee ee Meeeeeeeee eeee Meeeeeeeeeee[‌88‌,‌88‌]

Mee eeee eeeeeeee eee eee eeeeeeeee eeeeeeeeeeeeeeee eeeee eeeeeeeeeeee ee eee eeeeeeeeeee eee eeeeeeee ee eeee eeeee eee eeeeeeeee eeeeeee. Meeeeee[‌88‌,‌88‌] eee ee-eeeeeee eeee eeeeeeeee e eeeeeeee eee eee ee eeee eeeeeeeeee ee eeeeeeeeeeee ee eee eeeeeeee eeeeeeeeee ee M-eeeeee-M-eeeeeeeeeee (88) ee eee eeeeeeee ee eee eeeeeeeee eeeeeeee eee eee eeeeee (Meeeee 8).[‌88‌,‌88‌] Meee eeee eeeeeee eeeeee ee M-eeeeee-M-eeeeeeeeeee (88) ee eeeeeeeee ee eeee eeeee ee eeeeeee eeee eeeeee ee eeeeeeeeeeeeeee eeeeeeee 88.

Meeeee 8 Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeee ee Meeeeee eeee Me Meee Meeeeeeee Meeeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeee eeeeeeeeeeeeeeee ee eeeeeee eeeeeee eeee eeeeeeeeeeee eeeeeeeee ee eeeeeeeee(MM) eeeeeee eee ee eeeeeeeeeeee eeeee eeeeee eeeeeeeeeee. e-Meeeeeeee eeeeeeeeee 88,[‌88‌] Meeeeeeeʼe eeeeee eeeeeee 88,[‌88‌,‌88‌] eee eeeeee eeeeeee eeeeee 88[‌88‌‌88‌] eeee eeee eeeee ee eeeeeee eeee eeeeeeeeeeeeeeee (Meeeee 8).[‌88‌‌88‌] Meeeeeeeeeeeee eeeeee eee ee eeeeeeeee (ee ee 88.8% ee) ee eeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeee eeeeeeeeee ee eeeeeeee.

Mee eee ee e eeeeee eeeeeeee ee ee eeeeeeeeee eeeeeeeeeee ee eeeeeee eeeeeeeeeeeeeeee eeeeeeeeeeee-eeeee eeeeeeeeeeeeeeee. Mee eeeeee eeeeeeeee eeeeeeeee eeeeee ee eeee eeeeeeeeeee eeeeeee eee eeeeeeeeeeeeeeee eeeeeeee, eee eeee eeeeeee eeeeeeee ee eeeeeeee eeee eeee eeeeeeee.[‌88‌] Meeeeee ee eeeeeeee eeeeeeeeeeeeee ee eee eeeeee eeeeee eeeeee eee eeeeeeeee eeeeeee eeeeeeee eee eee eeee ee eeeeeeeeeeeeeeee.

Meeeee 8 Meeeee Meeeeeeeeee Meee ee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeee ee Meeeeee eeee Meeeeeeeeeee[‌88‌‌88‌]

Meeeee eeeee, eeeeeeeeeeee eeeeee(M) eeeeeeee eee eeeeee(M) eeeeeee, eeee eeeee eee eeeee eeeeeeeee eeee eee eee eeeeeeeeeeeeeeee ee eeeeeee eeee eeeeeeeeeeee.[‌88‌] Meeeeee, eeeeee-eeeee eeeeeeeee eeeeeee eee eeeeeeeeeeeee eeee eeeeeeeee eeee eeeee eeeee ee eeeeeeeee ee eeeee ee eeeeeeeee eeeee, eeeeeeeeeeeeeeee, eee eeeee. Meeeeeee, eee eee eeeeeeee eeeeeee eee eee eeeeeeeeeee ee eeeeeee ee eee eeeeeeee ee eeeeee eeeee, eee Meeeee–Meee eeeeeeeeeeeeeeee,[‌88‌] eeeeeeee eee eee eee eeeeeeee ee eeeeeeeee eeeeeee eeeeeeeeeeee. Meeeeeeeeeee, ee eeee eeeeeeeeeee eeeeeeee eee eee ee eee eeeeee-eeeee eeeeeeee eee eeee eeeee ee ee eeeeeeeeeeee eeeeeeee ee eee eee eeeee eeeeeeeee. Meee ee eeeeeeeeeeee eee eeee ee eee eeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeee (88) eeee eeeeeeeeeeee, eee eeeee eee eee ee eeeeeeeee(MM) eeeeeee ee eeeeeeee eeeeeee eee eeeeeeeeeeeeeee eeeeeeeeee 88 ee eee eeeee (88%) eeeeeeee eeee e eeeeeee ee eeeeeeeeeeee eeeeeee eeee eee eeeeee eeeeeeeee ee eeeeeee eeeeeeeee eeeee eeee eee eeeeeeeeeeee eeeeeeeeeeee 88 (Meeeee 8).[‌88‌] Meeeeee, ee eee eeeeeeee ee eeeeee(M) eeeeeeee, eeeeeeeeeeee 88 ee eeeeeeee ee eeee eeeee (88%) ee eee eeee eeeeeee.[‌88‌] Mee eeeeee/eeeeeeeeeeee eeeeee eee eeee eeee eeee ee eeeeeee eeee eeeeeee eeeeeeeee, eeee ee eee eeeeeeeeeeeeeeee eeee eeeeee [88]eeeeeeeeeee (M)-(−)-88 eeee (M)-88.[‌88‌]

Meeeee 8 Meeeeeeeeeeeeeee ee Meeeeeeeeeeeeeeeee Meeeeeeeeee eeee Meeeeeeeeeee eeeee Meeeeeeee eee Meeeee Meeeeeeee[‌88‌‌88‌]

Meeeee eeeeee eeeeeeeee eeeeeee eeeeeeeeee eee eee(eeeeeeeeeeeeee) eeeeeee eeee eeee eeee eee eeeeeeeeeeeeeeee eeeeeeeeeeeeeeee ee (M)-eeeeeeeee eeeee eeeeeeeeeee 88[‌88‌] eee 88[‌88‌] eeee eeeeeeeeeeee eeeee eee Meeeee–Meee eeeeeeee. Meeeeeee ee eeee eee eeee eeeeeeee eee eeeeeeeee eeeeeeeee, eeeeee ee eeee eeeeeee eeeeee eee eeee eeeeeeeeeeee eeeeee eee eeeeeeee eeee eee eeeeee eeeeee (Meeeee 88).[‌88‌,‌88‌]

Meeeee 88 Meeeeeeeeeeeeeee Meeeeeeeeeeeeeee ee Meeeeee eeee Meeeeeeeeeee Meeee Meeeee Meeeee Meeeeeeee[‌88‌,‌88‌]

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M8 ee (%) Meeee (%) Mee
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Me 8888, Meeeeeee eee Meeeeee eeeeeeee e eee eeeeee eeee eeeeeeeee eee eeee eee eeeeeeeee eee eeeeeeeeee ee eee eeeeeeeeeeeeeeee eeeeeeee eeee eeeeeeeeeeee.[‌88‌] Mee eeeeee eeeeeee eeeee-eeeeeee M-eeeeee-M-eeeeeeeeeeeeeeeeee 88 (Meeeeee), e eeeeee eee eeeeeeeeeeee eeeeeeeee eeeeeeee eeee eee eeeeeeee eeeeeeee ee eeeee eeeeeeeeeeee eeeeeeeeee. Meee eeeeeeeee eeee 8 M eeeeeee eeeeeeeee eeeeeeeee eeeeeeee, eee ee eeee eeeeeeeee eeeeeeeeeeee ee eeeeeeeeeee eeee eee eeeeeee eeeee ee eee eee-eeeee eeeeee, eeeee ee eee-eeeeee eeee(MMM)–eeeeeeeee eeeeeee eeeeeeee eee eeeeeeeeeeeee ee ee eeeeee. Mee eeeee ee eee eeeeeeee ee eeeee eee eeeeeeee 88 eee eeeeeeee ee eeee ee eeee eeeeee eeeee eeee 8 eee% ee eee eeee eeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeee Meeeeeeeeeee Meeeeeeeee/Meee-Meeeeeeee Meeeeeeeeeeeeeee[‌88‌]

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Meeeee 8-Meeeeeeeeeeeeeeee Meeeee (Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeeeeee ee eeeeeeeee ee eeeee, eeeeeeee, ee eeee eee ee eeeeee eeeee ee eeeeeeeeee.

Me eeeeeeee (8 e, 8.8 eeee) eee Me(MMe)8 (88 ee, 8.8888 eeee) ee Me8M (88 eM), e eeee ee MM8M8 ee Me8M [88 eM; eeeeeeee eeee M-eeeeee-M-eeeeeeeeeee (88; 8 e, 88 eeee)][‌88‌] eee eeeee eeeeeeee ee 8 °M eeee eeeeeeeeee eeeeeeee eeee 88 eee. Meeee eeeeeeeeeeeee ee eee eeee, eee eeeeeee eee eeeeeeeeeeeeeee [eeeeee eee (8 e), eeeeee]: eeeee: 8.88 e (88%); ee 88–88 °M.

Meeeeeeeeeeee 88; Meeeeee Meeeeeeee eee Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeee Meeee Me Meee Meeeeeeee Meeeeeeeeeee:[‌88‌]

Mee eeeeeeeeeee eeeeeeee (8.8 eee), eee eeeeeee (88–888 eM), eee 88% ee MMM (ee. 88 eM) eeee eeeeee ee e eeeee eeeeeeee eeee e eeeeeee, e eeeeeeeeeee eeeeeeee eeeeee, eee e eeeeee eeeeeeeee. Meee, eee eeeee eeeeeee ee M-eeeeee-M-eeeeeeeeeee (88; 8–8 e) eee Me-eeeee eeeeeeee (8.8 eeee) eeeeeeeee ee MM8Me8 (8 eM) eeee eeeee ee 88–88 °M. Meeeeeee ee eeeeeee eeeeeeee ee eeeee M-eeeeee-M-eeeeeeeeeee (88; ee. 8.8 e · eee−e; eeeee eeeeee 88–88 e, 8.88–8.88 eee) eee eeeeeee eee eeeee eee eeeee ee eee eeeeeeeee. Me eee eee ee eee eeeeeeee, eee eeeeeee eeeee eee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee eeeeee. Mee eeeeee eeeeeeee eeee eeeeeeee eeee eee eeeeeeee eeeeeee eeeee, eee eee eeeeeeeee eeee eee eeeeeeee eeeeeee eeeeeee, eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeeeeeee eeeeeeeeeeee.

(8M,8M,8M,8M,8M,8M,88M,88M,88M,88M,88M,88M)-Meeeeeeeeeeeee[]eeeeeeeeeeeee [(M)-(−)-88]; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeeeeee ee eeeeeeeee ee eeeee, eeeeeeee, ee eeee, eee ee eeeeee eeeee ee eeeeeeeeee.

M eeee ee MM8M8 ee Me8M [eeeeeeee eeee M-eeeeee-M-eeeeeeeeeee (88; 8.88 e, 88.8 eeee)][‌88‌] eee eeeee eeeeeeee ee ee ee e eeeeeeeeee eeeeeee eeeeeeeeee ee eee eeeeeeeeeeeeeeeeee eeeeeeeeee (M)-88 (88 ee, 8.888 eeee), MeMe (8.888 e, 88.88 eeee), eee Me(MMe)8 (888 ee, 8.888 eeee) ee Me8M (88 eM) eeee 8 e. Mee eeeeeee eee eeee eeeeeeee eeeeeee e eee ee Meeeee, eee, eeeee eeeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeee eee eeeeeee eeee eee eeee eeeeeeeeee ee eee eeeeeeee eeeee eeee eeeee. Meeeee eeeeeeeeeeeeee ee eee eeeee eeeeeee (eeeeee eee, eeeeee; Me 8.88) eeeeeeee e 8.8:8 eeeeeee ee eee eeeee eeeeeee eee eee eeeeeeee (8M,8M,8M,8M,8M,8M,88M,88M,88M,88M,88M,88M)-88; eeeee: 88 ee (88%). Meee eeeeeeee eeeeeeee [8 ee (88%)] eee eeee eeeeeeeee. Mee eeeeeeeeeeee eeee eeeeeeeee ee eeeeeeeeeee MMMM ee eeee eeeeeeeee eeeeee ee (8M,8M,8M,8M,8M,8M,88M,88M,88M,88M,88M,88M)-88; eeeee: 88 ee (88%); eee (M)-(−)-88; eeeee: 88 ee (88%). Meeeeeeeee eeeeeee eeee eeeeeeee ee eeeeeeeeeeeeeeeee (MeMM). (M)-(−)-88 eeeeee eeeeeeee eeeee 888 °M; ee 888 °M; [α]M88 −8888.8 (e 8.888, MMMe8).

Meeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: M-Meeeee-M-eeeeeee-8-eeeeeeeeeeeeeeeeee (M,8-eeeeeeee-M-eeeeeeeeeeeeeeeeeeeeeeeee, Meeeeee) eeeeeeeee eeeeeeeee eee eeeee eeeeeeeeeeee eeee eeeeeee eeee eeeeeee.

Meeeee(8,88,88,88-eeeeeeeeeeeeeeeeeeeeeee)eeee(MMM) (8–8 eee%) eee eeeeeeeee ee eee eeeeee eeeeeeeee (8.88 eeee) eee 8 M ee MMM eee eeeee ee ee eeee eeee. Me eeee eeeeeeeeee, eeeeeeee eeeeeee eeee (>8888 eee) eee eeeee 8.88 M ee eeeeee 8-(M-eeeeee-M-eeeeeeeeeeeeeeee)eeeeeeee[‌88‌] (88, Meeeeee; 8–8 eeeee) ee ee eeee e eeeeeee eeee. Meeee e eeeeeee 88 eee, eee eeee eee eeeeeee eeee M8M eee eeeeeeeee eeee MM8Me8 (8 ×). Mee eeeeeee eeeeee eeee eeeee (MeMM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeee MMM eeeeeeee ee eee eeeee eeeeeee, eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeeee/Me8M) ee eeeeee eee eeee eeeeeee.