AI Article Synopsis
- The study introduces a new reaction method for adding pentafluorosulfanyl groups to terminal alkynes using specific chemicals and light to initiate the process.
- This reaction selectively produces a new type of isomer called (Z)-(1-alken-1-yl)pentafluoro-λ-sulfanes with a high ratio of Z to E isomers.
- Computational analysis suggests that the preference for the Z isomer arises from the natural tendency of the radicals formed during the reaction to adopt a cis orientation, alongside steric factors affecting the transition state for E products.
Article Abstract
A photoinitiated anti-hydropentafluorosulfanylation of terminal alkynes using SF Cl and (TMS) SiH as the hydrogen atom donor is reported. This transformation generates selectively (Z)-(1-alken-1-yl)pentafluoro-λ -sulfanes (Z:E : >85:15), thus allowing the preparation of this previously unknown geometrical isomer. DFT calculations highlight that the selectivity is due to the intrinsic preference of SF -substituted vinylic radicals to adopt a cis geometry, and to increased steric contacts during the transition structures leading to the minor (E)-products.
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| http://dx.doi.org/10.1002/anie.202112575 | DOI Listing |
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Photoinitiated anti-Hydropentafluorosulfanylation of Terminal Alkynes.
Angew Chem Int Ed Engl
January 2022
CCVC, PROTEO, Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, G1V 0A6, Canada.
Article Synopsis
- The study introduces a new reaction method for adding pentafluorosulfanyl groups to terminal alkynes using specific chemicals and light to initiate the process.
- This reaction selectively produces a new type of isomer called (Z)-(1-alken-1-yl)pentafluoro-λ-sulfanes with a high ratio of Z to E isomers.
- Computational analysis suggests that the preference for the Z isomer arises from the natural tendency of the radicals formed during the reaction to adopt a cis orientation, alongside steric factors affecting the transition state for E products.
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