Cyclopropyl activation of adjacent methylene groups in spiro[2.n]alkanes and bicyclo[n.1.0]alkanes

Charles Roberts; John C. Walton

doi:10.1039/c39840001109

Cyclopropyl activation of adjacent methylene groups in spiro[2.n]alkanes and bicyclo[n.1.0]alkanes

Charles Roberts, John C. Walton^*

^*Corresponding author for this work

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

Abstract

The hydrogens at C(2) in spiro[2.n]alkanes are abstracted about five times more rapidly than 'normal' secondary hydrogens by t-butoxyl radicals, because of favourable overlap of the p-orbital at C(2) with the HOMO of the adjacent cyclopropyl ring; the hydrogens at C(2) in bicyclo[n.1.0]alkanes are less activated because the cyclopropyl ring orientation is less favourable for overlap.

Original language	English
Pages (from-to)	1109-1111
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	16
DOIs	https://doi.org/10.1039/c39840001109
Publication status	Published - 1 Jan 1984

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title = "Cyclopropyl activation of adjacent methylene groups in spiro[2.n]alkanes and bicyclo[n.1.0]alkanes",

abstract = "The hydrogens at C(2) in spiro[2.n]alkanes are abstracted about five times more rapidly than 'normal' secondary hydrogens by t-butoxyl radicals, because of favourable overlap of the p-orbital at C(2) with the HOMO of the adjacent cyclopropyl ring; the hydrogens at C(2) in bicyclo[n.1.0]alkanes are less activated because the cyclopropyl ring orientation is less favourable for overlap.",

author = "Charles Roberts and Walton, \{John C.\}",

year = "1984",

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doi = "10.1039/c39840001109",

language = "English",

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journal = "Journal of the Chemical Society, Chemical Communications",

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T1 - Cyclopropyl activation of adjacent methylene groups in spiro[2.n]alkanes and bicyclo[n.1.0]alkanes

AU - Roberts, Charles

AU - Walton, John C.

PY - 1984/1/1

Y1 - 1984/1/1

N2 - The hydrogens at C(2) in spiro[2.n]alkanes are abstracted about five times more rapidly than 'normal' secondary hydrogens by t-butoxyl radicals, because of favourable overlap of the p-orbital at C(2) with the HOMO of the adjacent cyclopropyl ring; the hydrogens at C(2) in bicyclo[n.1.0]alkanes are less activated because the cyclopropyl ring orientation is less favourable for overlap.

AB - The hydrogens at C(2) in spiro[2.n]alkanes are abstracted about five times more rapidly than 'normal' secondary hydrogens by t-butoxyl radicals, because of favourable overlap of the p-orbital at C(2) with the HOMO of the adjacent cyclopropyl ring; the hydrogens at C(2) in bicyclo[n.1.0]alkanes are less activated because the cyclopropyl ring orientation is less favourable for overlap.

UR - https://www.scopus.com/pages/publications/1242268902

U2 - 10.1039/c39840001109

DO - 10.1039/c39840001109

M3 - Article

AN - SCOPUS:1242268902

SN - 0022-4936

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JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

IS - 16

ER -

Cyclopropyl activation of adjacent methylene groups in spiro[2.n]alkanes and bicyclo[n.1.0]alkanes

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