Welcome to LookChem.com Sign In|Join Free

Article Doi

Cyclisation of ω-(Isocyanatocarbonyl)alkyl Radicals: Acyclic Precursors of Imidyl Radicals

DOI: 10.1039/P29890001559

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1559 - 1568 (1989)

Update date:2022-08-03

Topics:

Authors:

Kaushal, ParveenKaushal, Parveen

Roberts, Brian P.Roberts, Brian P.

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P29890001559

Imidyl radicals, generated by photolysis of, or halogen-atom abstraction from, N-halogenoimides, are efficiently trapped by But2C=CH2 to give relatively persistent adducts which have been studied by e.s.r. spectroscopy.Bromine-atom abstraction from BrCH2CH2C(O)NCO (2) yields (1) which undergoes rapid 1,5-endo cyclisation to give the succinimidyl radical.This cyclisation has been investigated using e.s.r. spectroscopy in conjunction with spin-trapping by But2C=CH2 and ButN=O.The rate coefficient for cyclisation of (1) has been estimated to be 3.7 * 106 s-1 at 328 K in cyclohexane from analysis of the products from the radical-chain reaction between (2) and triethylgermane.E.s.r. and product-analysis studies show that (14) cyclises, more rapidly than (1), to give the 2,2-dimethylsuccinimidyl radical which subsequently undergoes ring opening to yield (15).The overall rearrangement of (14) to (15) represents a 1,2-shift of the -C(O)NCO group via an intermediate imidyl radical.The glutarimidyl radical is formed by 1,6-endo cyclisation of .It is proposed that the rapid cyclisation of ω-isocyanatoalkyl radicals provides strong evidence that the unpaired electron occupies a ?-orbital in the product imidyl radicals.

View More

Products guided by the article

Product name:propionyl isocyanate

Cas No:4382-03-0

4382-03-0

R&D Labs maybe for 4382-03-0

  • Guangzhou Chemical Reagent Factory

    Contact:+86-20-8435 9820 or 8435 7345

    Address:Southern Guangzhou, Guangdong, China

  • Second Pharma Co., Ltd

    Contact:+86-575-82733999 0575-82732999

    Address:hangzhou gulf fine chemical zone,shangyu city,zhejiang province

  • Beijing eternalchem Co,. Ltd

    Contact:+86-10-59484199

    Address:No.58-A1026 Liangguan Street

  • Hangzhou Chemfar Ltd.

    Contact:+86-571-87859231, 87859237, 87859239

    Address:1606,Huarong Times Mansion, No.3880 Jiangnan Avenue, Binjiang District, Hangzhou, China, 310053

  • Second Pharma Co., Ltd

    Contact:+86-575-82733999 0575-82732999

    Address:hangzhou gulf fine chemical zone,shangyu city,zhejiang province

Relevant to this article

Hot Product