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Steric effects on the regio- and stereospecificity of the nucleophilic addition of alcohols to 1 -alkynes

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    In the nucleophilic addition of alcohols to alkylacetylenes (methyl- and tert-butyl-), theα regiospecificity of the attack of alkoxide converts toβ regiose lectivity with the increasing steric requirements of the substituent in the alkyne and of the attacking nucleophile.

  2. 2.

    The reaction leading to theβ adduct takes place with strict steric specificity by a nucleophilic mechanism of 1, 2-anti-addition with the formation of cis isomers; this behavior is independent of steric hindrances.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    V. I. Laba, A. A. Kron & E. N. Prilezhaeva

Authors
  1. V. I. Laba
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  2. A. A. Kron
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  3. E. N. Prilezhaeva
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Additional information

For the previous communication in this series, see our earlier work [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1546–1552, July, 1976.

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Laba, V.I., Kron, A.A. & Prilezhaeva, E.N. Steric effects on the regio- and stereospecificity of the nucleophilic addition of alcohols to 1 -alkynes. Russ Chem Bull 25, 1470–1475 (1976). https://doi.org/10.1007/BF00920821

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  • DOI: https://doi.org/10.1007/BF00920821

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