Synthesis and applications of alkenyl chlorides (vinyl chlorides): a review

• Daniel S. Müller

Beilstein J. Org. Chem. 2026, 22, 1–63, doi:10.3762/bjoc.22.1

• -dichloroethylene) to achieve selective monocoupling reactions catalyzed by nickel with Grignard reagents (Scheme 51C) [176]. Building on Sonogashira's findings [177], Linstrumelle also documented the first monoselective coupling of 1,2-dichloroethylenes with alkynes using palladium catalysis (Scheme 51C). Organ

• demonstrated that the use of 4 equivalents of 1,1-dichloroethylene in combination with XPhos or JohnPhos ligands enabled monoselective cross-coupling with alkenyl- and arylboronic acids (Scheme 54B) [184]. Though mechanistically not related it is noteworthy that diazonium salts couple efficiently with alkenyl

• alkenyl chloride product was favored by the utilization of a large excess (100 equivalents) of (E)-1,2-dichloroethylene in the presence of the Grela catalyst 290 [190]. Depending on the substrate, stereoselectivity and yields can vary significantly (Scheme 56). A subsequent study by Johnson confirmed

1,2-Difluoroethylene (HFO-1132): synthesis and chemistry

• Liubov V. Sokolenko,
• Taras M. Sokolenko and
• Yurii L. Yagupolskii

Beilstein J. Org. Chem. 2024, 20, 1955–1966, doi:10.3762/bjoc.20.171

• catalyst (Pd, Pd, Pt, Rh, Ru, Ir, Ni/Cu, Ag, Au, Zn, Cr, Co, Scheme 5) [62][63]. Further, 1,2-Dichloroethylene was reacted with hydrogen fluoride in the presence of metal fluorides or transition metals (Cr, Al, Co, Mn, Ni, Fe) to form 1,2-difluoroethylene (Scheme 6) [56][58]. In patents [59][60], an exotic

• -Difluoroethylene synthesis from HFO-1123. 1,2-Difluoroethylene synthesis from CFC-112 and HCFC-132. 1,2-Difluoroethylene synthesis from HFC-143. 1,2-Difluoroethylene synthesis from HCFC-142 via HCFC-142a. 1,2-Difluoroethylene synthesis from CFO-1112. 1,2-Difluoroethylene synthesis from 1,2-dichloroethylene. 1,2

High-speed C–H chlorination of ethylene carbonate using a new photoflow setup

• Takayoshi Kasakado,
• Takahide Fukuyama,
• Tomohiro Nakagawa,
• Shinji Taguchi and
• Ilhyong Ryu

Beilstein J. Org. Chem. 2022, 18, 152–158, doi:10.3762/bjoc.18.16

• small amount of undesired 1,2-dichloroethylene carbonate (2’) was detected by GC (Table 1, entry 2). When 0.45 equiv of Cl2 was used, the conversion of 1 increased to 21% and the selectivity of 2 became 91% (Table 1, entry 3). The reaction of 1 with one equivalent of Cl2 gave 2 and 2’ in a ratio of 89

Learning from B₁₂ enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

• Keishiro Tahara,
• Ling Pan,
• Toshikazu Ono and
• Yoshio Hisaeda

Beilstein J. Org. Chem. 2018, 14, 2553–2567, doi:10.3762/bjoc.14.232

• −1.4 V vs Ag/AgCl in the presence of 1 in DMF/n-Bu4NClO4. The DDT was converted to 1,1-bis(4-chlorophenyl)-2,2-dichloroethane (DDD), 1,1-bis(4-chlorophenyl)-2,2-dichloroethylene (DDE), 1-chloro-2,2-bis(4-chlorophenyl)ethylene (DDMU), and 1,1,4,4-tetrakis(4-chlorophenyl)-2,3-dichloro-2-butene (TTDB, E/Z

Anionic cascade reactions. One-pot assembly of (Z)-chloro-exo-methylenetetrahydrofurans from β-hydroxyketones

• István E. Markó and
• Florian T. Schevenels

Beilstein J. Org. Chem. 2013, 9, 1319–1325, doi:10.3762/bjoc.9.148

• original and connective anionic cascade sequence is reported. Base-catalysed condensation of β-hydroxyketones with 1,1-dichloroethylene generates, in moderate to good yields, the corresponding (Z)-chloro-exo-methylenetetrahydrofurans. Acidic treatment of this motif leads to several unexpected dimers

• , possessing unique structural features. Keywords: acetylene addition; dichloroethylene; dimerisation; dioxanes; tetrahydrofurans; Introduction Recently, we have shown that simple ketones reacted with 1,1-dichloroethylene, in the presence of potassium tert-butoxide, to afford rare (Z)-chloro-exo

• -dichloroethylene is converted into the corresponding chloro-acetylene anion 9 [4][5]. This nucleophilic species adds rapidly, though reversibly, to acetone, leading ultimately to the formation of 5. However, in this case, competitive aldol reaction appears to take place, delivering the adduct 8. The subsequent

Chemistry of polyhalogenated nitrobutadienes, 10: Synthesis of highly functionalized heterocycles with a rigid 6-amino-3-azabicyclo[3.1.0]hexane moiety

• Viktor A. Zapol’skii,
• Jan C. Namyslo,
• Armin de Meijere and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2012, 8, 621–628, doi:10.3762/bjoc.8.69

• stabilized by an intramolecular hydrogen bridge bond in a six-membered pseudocycle (Figure 3). Upon treatment of 1,3-dinitro-1,4,4-trichlorobutadiene (4), which was obtained in a four-step sequence from 1,2-dichloroethylene (mixture of diastereomers) [20][21], with a fourfold excess of the azabicyclo[3.1.0