Generation, trapping and fate of alkylidenecarbene-iodonium ylides from the addition of NaN3 to alkynylphenyliodonium tosylates

✍ Scribed by Tsugio Kitamura; Peter J. Stang

• Book ID: 104217512
• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 170 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)82069-9

✦ Synopsis

Addition of NaW to RC=_CfPh*OTs results in novel alkylidenecarbene-iodonium ylides. 5, R(N )C-C=IPh. that ay either protonatlon, ylide transfer or insertion of the derived carbene K(N3)&: give unique functionalized vinyl azides. Despite the importance of ylidet, I. in carbene chem1stry.I until recently2 there was little known about these species. In the last few years they have become the object of increasing research effort with particular attention on halonium ylides.3 In 1984 Moriarty and co-workers4 reported the x-ray structure of a stable carbene-iodonium ylide 2.