Cited by 46Synthesis and Reactivity of Sulfur-Containing CompoundsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques

Tributylstannane-mediated cyclization of thionocarboxylic acid derivatives

Bachi, Mario D., Bosch, Eric, Denenmark, Daniella, Girsh, Diana·1992·The Journal of Organic Chemistry

Abstract

Cyclization reactions of various thionoesters and thioamides involving the addition of tri-n-butylstannyl radical to a thiocarbonyl group and intramolecular addition of the resulting radical to a carbon-carbon multiple bond was studied. Dithiocarbonate and (imidazolyl)thiocarbonyl derivatives of homoallylic alcohols gave α-substituted γ-thionobutyrolactones. The reaction is highly dependent on the substitution pattern on the double bond, a high yield of cyclic products being obtained only when the double bond is activated and unhindered. (Z)-4-Phenylbut-3-enyl thionobenzoate afforded 4,5-dihydro-2-phenyl-3-benzylfuran in low yield. In reactions involving a thioamide group, good yields of cyclic products were obtained only from compounds in which the electron density on the nitrogen atom is decreased by an electron attracting group. Cyclization of 1-((E)-4-phenylbut-3-en-1-yl)-5-thioxopyrrolidin-2-one (23) afforded 1-aza-4-benzylbicyclo[3.3.0]oct-4-en-8-one (33).

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Crossref · 10.1021/jo00051a024

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Authors
Bachi, M. D., Bosch, E., Denenmark, D., & Girsh, D.
Venue
The Journal of Organic Chemistry
Published
1992-12
Volume
57
Issue
25
Pages
6803-6810
ISSN
  • 0022-3263 (ISSN-L)
  • 1520-6904
OpenAlex
W2952239491
Cited by
46
References
0
Citations by year
2025: 1 · 2023: 1 · 2021: 2 · 2020: 1 · 2018: 1 · 2017: 2 · 2015: 1 · 2012: 1
FWCI
2.63
Type
journal article
Language
en
Open access
closed
Locations
  • The Journal of Organic Chemistry (publishedVersion)
  • BearWorks (Missouri State University) (submittedVersion)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Reactivity of Sulfur-Containing Compounds
  • Physical Sciences › Chemistry › Organic Chemistry › Radical Photochemical Reactions
  • Physical Sciences › Chemistry › Organic Chemistry › Sulfur-Based Synthesis Techniques
Keywords
tributylstannane, thioamides, radical cyclization, intramolecular radical addition, xanthates, homoallylic alcohols, furan formation

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