Effect of conformation and stereochemistry in substitution reactions of fused chlorocyclobutanones: oxyallyl cation intermediates

Alfred Hassner; John L. Dillon; Larry R. Krepski; Kay D. Onan

doi:10.1016/s0040-4039(00)86385-6

Effect of conformation and stereochemistry in substitution reactions of fused chlorocyclobutanones: oxyallyl cation intermediates

Alfred Hassner, John L. Dillon, Larry R. Krepski, Kay D. Onan

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

17 Scopus citations

Abstract

Fused α-acyloxycyclobutanones, whose conformation and stereochemistry have been unambiguously established by X-ray analysis, undergo an unusual displacement with methoxide as nucleophile to produce α-methoxycyclobutanones. The success of this reaction, which suggests the intermediacy of an oxyallyl cation, is highly dependent on conformational and steric factors.

Original language	English
Pages (from-to)	1135-1138
Number of pages	4
Journal	Tetrahedron Letters
Volume	24
Issue number	11
DOIs	https://doi.org/10.1016/s0040-4039(00)86385-6
State	Published - 1983
Externally published	Yes

Bibliographical note

Funding Information:
This research was supported by the DHEW Grant CA-19203 from the NC1 and a

Funding

This research was supported by the DHEW Grant CA-19203 from the NC1 and a

Funders	Funder number
NC1

Access to Document

10.1016/s0040-4039(00)86385-6

Cite this

@article{a00e3fee076b4319b17fa0ee8f2cd0d0,

title = "Effect of conformation and stereochemistry in substitution reactions of fused chlorocyclobutanones: oxyallyl cation intermediates",

abstract = "Fused α-acyloxycyclobutanones, whose conformation and stereochemistry have been unambiguously established by X-ray analysis, undergo an unusual displacement with methoxide as nucleophile to produce α-methoxycyclobutanones. The success of this reaction, which suggests the intermediacy of an oxyallyl cation, is highly dependent on conformational and steric factors.",

author = "Alfred Hassner and Dillon, {John L.} and Krepski, {Larry R.} and Onan, {Kay D.}",

note = "Funding Information: This research was supported by the DHEW Grant CA-19203 from the NC1 and a",

year = "1983",

doi = "10.1016/s0040-4039(00)86385-6",

language = "אנגלית",

volume = "24",

pages = "1135--1138",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "11",

}

TY - JOUR

T1 - Effect of conformation and stereochemistry in substitution reactions of fused chlorocyclobutanones

T2 - oxyallyl cation intermediates

AU - Hassner, Alfred

AU - Dillon, John L.

AU - Krepski, Larry R.

AU - Onan, Kay D.

N1 - Funding Information: This research was supported by the DHEW Grant CA-19203 from the NC1 and a

PY - 1983

Y1 - 1983

N2 - Fused α-acyloxycyclobutanones, whose conformation and stereochemistry have been unambiguously established by X-ray analysis, undergo an unusual displacement with methoxide as nucleophile to produce α-methoxycyclobutanones. The success of this reaction, which suggests the intermediacy of an oxyallyl cation, is highly dependent on conformational and steric factors.

AB - Fused α-acyloxycyclobutanones, whose conformation and stereochemistry have been unambiguously established by X-ray analysis, undergo an unusual displacement with methoxide as nucleophile to produce α-methoxycyclobutanones. The success of this reaction, which suggests the intermediacy of an oxyallyl cation, is highly dependent on conformational and steric factors.

UR - http://www.scopus.com/inward/record.url?scp=0039143003&partnerID=8YFLogxK

U2 - 10.1016/s0040-4039(00)86385-6

DO - 10.1016/s0040-4039(00)86385-6

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:0039143003

SN - 0040-4039

VL - 24

SP - 1135

EP - 1138

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

Effect of conformation and stereochemistry in substitution reactions of fused chlorocyclobutanones: oxyallyl cation intermediates

Abstract

Bibliographical note

Funding

Access to Document

Other files and links

Fingerprint

Cite this