HMPA-Mediated conjugate addition of alkyl- and phenylthioallyl anions to cyclopentenone

Malcolm R. Binns; Richard K. Haynes; Timothy L. Houston; W. Roy Jackson

doi:10.1016/S0040-4039(01)85560-X

HMPA-Mediated conjugate addition of alkyl- and phenylthioallyl anions to cyclopentenone

Malcolm R. Binns^*, Richard K. Haynes, Timothy L. Houston, W. Roy Jackson

^*Corresponding author for this work

Research output: Contribution to journal › Journal Article › peer-review

50 Citations (Scopus)

Abstract

One equivalent of HMPA induces 1,4-addition of the title anions predominantly through the α-position to cyclopentenone in THF at -78°. In THF alone irreversible addition takes place to give mixtures comprising largely α and γ-1,2 products.

Original language	English
Pages (from-to)	573-576
Number of pages	4
Journal	Tetrahedron Letters
Volume	21
Issue number	6
DOIs	https://doi.org/10.1016/S0040-4039(01)85560-X
Publication status	Published - 1980
Externally published	Yes

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@article{27068905cffb46a19b82f14689228a2d,

title = "HMPA-Mediated conjugate addition of alkyl- and phenylthioallyl anions to cyclopentenone",

abstract = "One equivalent of HMPA induces 1,4-addition of the title anions predominantly through the α-position to cyclopentenone in THF at -78°. In THF alone irreversible addition takes place to give mixtures comprising largely α and γ-1,2 products.",

author = "Binns, \{Malcolm R.\} and Haynes, \{Richard K.\} and Houston, \{Timothy L.\} and Jackson, \{W. Roy\}",

year = "1980",

doi = "10.1016/S0040-4039(01)85560-X",

language = "English",

volume = "21",

pages = "573--576",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "6",

}

TY - JOUR

T1 - HMPA-Mediated conjugate addition of alkyl- and phenylthioallyl anions to cyclopentenone

AU - Binns, Malcolm R.

AU - Haynes, Richard K.

AU - Houston, Timothy L.

AU - Jackson, W. Roy

PY - 1980

Y1 - 1980

N2 - One equivalent of HMPA induces 1,4-addition of the title anions predominantly through the α-position to cyclopentenone in THF at -78°. In THF alone irreversible addition takes place to give mixtures comprising largely α and γ-1,2 products.

AB - One equivalent of HMPA induces 1,4-addition of the title anions predominantly through the α-position to cyclopentenone in THF at -78°. In THF alone irreversible addition takes place to give mixtures comprising largely α and γ-1,2 products.

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:A1980JE07200023

UR - https://www.scopus.com/pages/publications/0344184960

U2 - 10.1016/S0040-4039(01)85560-X

DO - 10.1016/S0040-4039(01)85560-X

M3 - Journal Article

SN - 0040-4039

VL - 21

SP - 573

EP - 576

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 6

ER -

HMPA-Mediated conjugate addition of alkyl- and phenylthioallyl anions to cyclopentenone

Abstract

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