Preparation of mono- and diiodocyclopropene

Structure, Synthesis, and Chemical Reactions of Fluorinated Cyclopropanes and Cyclopropenes

“…In a later report, Sepiol and Soulen reported the preparation of 1,2-diodo-3,3-difluorocyclopropene (97) as well as the 1-chloro-and 1-bromo-2-iodo-3,3-difluorocyclopropenes, 98 and 99. 195 Reductive removal of the iodine in 98 by means of sodium trimethoxyborohydride provided the trihalogenated cyclopropene 100. 196 Since the minor product 95 from treatment of tetrachlorocyclopropene with antimony trifluoride is less volatile than the major product 94, it is possible to separate the two by distillation, but the monofluoro cyclopropene prepared by this route is usually contaminated by the difluoro component.…”

Synthesis of Benzotriazine and Aryltriazene Derivatives Starting from 2‐Azidobenzonitrile Derivatives

“…64-65°C (ref. [39] 62-63°C). IR 2-Amino-6-methylbenzonitrile (6i): [40,41] This compound was prepared from 2-methyl-6-nitrobenzonitrile (2.0 g, 12.3 mmol) as according to ref.…”

“…This compound was prepared from 2-amino-4,6-dimethylbenzonitrile (6h; [39] 4.0 g, 27.4 mmol) according to ref. [32] The product was obtained as a yellow solid (3.56 …”

Eliminations Involving Carbon–Halogen Bonds and Leading to Highly Strained Rings

“…In the last case, both cis-and trans-diiodides reacted at similar rates, but while the cis-isomer reacted also with the related reagent diethylphosphite and triethylamine to give the cyclopropene in 20 h at 20 • C, the trans-iso-mer remained largely unchanged under these conditions. * The use of zinc in ethanol to 1,2-dehalogenate 1,2-dichlorotetraflurocyclopropane has been known for some time 59 The 1,2-dehalogenation reaction is also successful with 1,1,2-trihalo- (56) or 1,1,2,2-tetrahalocyclopropanes (57) and, in the former case, provides a valuable entry to 1-halcyclopropenes which often undergo ready lithium-halogen exchange to produce synthetically valuable 1-lithiocyclopropenes. The elimination occurs extremely rapidly when X = Br even at −95 • C. When X = Cl and Y = Br, the reaction occurs in a few minutes at a temperature of −40 • C, whereas with X = Y = Cl, the reaction occurs at a reasonable rate only at ambient temperature 111,112,84,87 .…”