Addition of nitrosyl chloride to olefins. Synthesis of some chloro ketones

Addition of NOCl to cyclic vinylsilanes: an unexpected reversal of regiochemistry

“…The formation of dichloronitroso compounds 13-17 is a consequence of isomerization of the primary adducts to the respective a-chlorooximes which are known to produce dichloronitroso compounds when treated with NOCl or hydrolyze to chloroketones if water is present. 14,15 We have confirmed that the dimers 7 and 9-11 give the secondary products when treated with NOCl. We have been able to isolate chlorooxime 26 from 10 under aqueous conditions.…”

Organic Reactions in the Solid State: Reactions of Enclathrated 3,4-Epoxycyclopentanone (=6-Oxobicyclo[3.1.0]hexan-3-one) in Tri-o-thymotide and Absolute Configuration of 4-Hydroxy- and 4-Chlorocyclopent-2-en-1-one

“…The residue was distilled under reduced pressure to yield 3 (2.25 g, 72%). Pale yellow liquid, unstable at r.t. [7]. B.p.…”

“…Crystal Structure of TOT/4-Hydroxycyclopent-2-en-1-one (2) and Absolute Configuration of the Guest. ± The 4-chlorocyclopent-2-en-1-one (3) has already been described [7], but its chiroptical properties remained unknown until now. The isolation of optically active 3 as sole product from the reaction of TOT/1 was not possible as pointed out above.…”

C-Nitroso Compounds

“…From the products iso lated, it may be inferred that cyclopentadiene adds nitrosyl chloride in a 1,4manner in moderate yields [55]. From the products iso lated, it may be inferred that cyclopentadiene adds nitrosyl chloride in a 1,4manner in moderate yields [55].…”

“…54).NO(4) Nitrosation of pyrimidines and aminouracil[105][106][107] (Eqs 55,56)[105][106][107] (Eqs 55,56)…”