Reagent-Specific Electrostatic Effects on Electrophilic π-Facial Stereoselectivity. Interpretation of the Stereochemical Variation of Electrophilic Additions to 7-Isopropylidenebenzonorbornenes

Yun Dong Wu; Yi Li; Jim Na; K. N. Houk

doi:10.1021/jo00069a025

Reagent-Specific Electrostatic Effects on Electrophilic π-Facial Stereoselectivity. Interpretation of the Stereochemical Variation of Electrophilic Additions to 7-Isopropylidenebenzonorbornenes

Yun Dong Wu, Yi Li, Jim Na, K. N. Houk^*

^*Corresponding author for this work

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

37 Citations (Scopus)

Abstract

Electrostatic interactions account for the stereochemical variations in electrophilic additions to 7-isopropylidenebenzonorbornenes. Different electrophilic reagents have very different electrostatic profiles. This conclusion is supported by electrostatic potential analyses of 7-methylenenorbornene and 7-methylenebenzonorbornene or by calculations on the interactions of point charges with the two faces of the π system.

Original language	English
Pages (from-to)	4625-4628
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	58
Issue number	17
DOIs	https://doi.org/10.1021/jo00069a025
Publication status	Published - 1993
Externally published	Yes

Access to Document

10.1021/jo00069a025

Cite this

@article{4432362077ed4aea99b5d187cffa081f,

title = "Reagent-Specific Electrostatic Effects on Electrophilic π-Facial Stereoselectivity. Interpretation of the Stereochemical Variation of Electrophilic Additions to 7-Isopropylidenebenzonorbornenes",

abstract = "Electrostatic interactions account for the stereochemical variations in electrophilic additions to 7-isopropylidenebenzonorbornenes. Different electrophilic reagents have very different electrostatic profiles. This conclusion is supported by electrostatic potential analyses of 7-methylenenorbornene and 7-methylenebenzonorbornene or by calculations on the interactions of point charges with the two faces of the π system.",

author = "Wu, \{Yun Dong\} and Yi Li and Jim Na and Houk, \{K. N.\}",

year = "1993",

doi = "10.1021/jo00069a025",

language = "English",

volume = "58",

pages = "4625--4628",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

}

Reagent-Specific Electrostatic Effects on Electrophilic π-Facial Stereoselectivity. Interpretation of the Stereochemical Variation of Electrophilic Additions to 7-Isopropylidenebenzonorbornenes. / Wu, Yun Dong; Li, Yi; Na, Jim et al.
In: Journal of Organic Chemistry, Vol. 58, No. 17, 1993, p. 4625-4628.

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

TY - JOUR

T1 - Reagent-Specific Electrostatic Effects on Electrophilic π-Facial Stereoselectivity. Interpretation of the Stereochemical Variation of Electrophilic Additions to 7-Isopropylidenebenzonorbornenes

AU - Wu, Yun Dong

AU - Li, Yi

AU - Na, Jim

AU - Houk, K. N.

PY - 1993

Y1 - 1993

N2 - Electrostatic interactions account for the stereochemical variations in electrophilic additions to 7-isopropylidenebenzonorbornenes. Different electrophilic reagents have very different electrostatic profiles. This conclusion is supported by electrostatic potential analyses of 7-methylenenorbornene and 7-methylenebenzonorbornene or by calculations on the interactions of point charges with the two faces of the π system.

AB - Electrostatic interactions account for the stereochemical variations in electrophilic additions to 7-isopropylidenebenzonorbornenes. Different electrophilic reagents have very different electrostatic profiles. This conclusion is supported by electrostatic potential analyses of 7-methylenenorbornene and 7-methylenebenzonorbornene or by calculations on the interactions of point charges with the two faces of the π system.

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:A1993LW05800025

UR - https://www.scopus.com/pages/publications/1542752284

U2 - 10.1021/jo00069a025

DO - 10.1021/jo00069a025

M3 - Journal Article

SN - 0022-3263

VL - 58

SP - 4625

EP - 4628

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

Reagent-Specific Electrostatic Effects on Electrophilic π-Facial Stereoselectivity. Interpretation of the Stereochemical Variation of Electrophilic Additions to 7-Isopropylidenebenzonorbornenes

Abstract

Access to Document

Other files and links

Fingerprint

Cite this