Generation of Iminyl Radicals through Sulfanyl Radical Addition to Vinyl Azides

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 5846-5848

  Montevecchi, Pier Carlo ^a   Navacchia, Maria Luisa ^a   Spagnolo, Piero ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001626827     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970691q     Document Type: Article

References (23)

1. For a recent review on sulfanyl radical additions to alkenes see: Chatgilialoglu, C.; Guerra, M. Supplement S: The Chemistry of Sulfur-containing Functional Groups; Patai, S., Rappoport, Z., Eds.; J. Wiley: Chichester, 1993; Ch. 8.
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11. Thiol 2a quantitatively reacted with phenylacetylene (10 equiv) in benzene solution at room temperature over ca. 30 min to give a 90: 10 Z/E mixture of styrene adducts [PhSCH=CHPh]. For a previous report of radical reactions of thiol 2a with alkynes, including phenylacetylene, see: Benati, L.; Montevecchi, P. C.; Spagnolo, P. J. Chem. Soc., Perkin Trans. 1 1991, 2103, and references cited therein.-
12. The lower reactivity of alkanethiols 2c,d clearly resulted from their higher S-H bond strength.
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