Cine substitution in fused chlorocyclobutanones by N, S and C nucleophiles. Oxyallyl cations and an unusual diner formation.

Alfred Hassner; Simha Naidorf-Neir; Hugo E. Gottlieb

doi:10.1016/0040-4039(90)80103-s

Cine substitution in fused chlorocyclobutanones by N, S and C nucleophiles. Oxyallyl cations and an unusual diner formation.

Alfred Hassner
, Simha Naidorf-Neir
, Hugo E. Gottlieb

Department of Chemistry

Bar-Ilan University

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

14 Scopus citations

Abstract

Chlorocyclobutanone 1 was shown for the first time to react with S-, N-, and C-nucleophiles to produce cine substitution products, which apparently arise via an oxyallyl cation species 2. With some nucleophiles, the cine product is accompanied by an unusual dimer involving bond formation between two tertiary carbons.

Original language	English
Pages (from-to)	2181-2184
Number of pages	4
Journal	Tetrahedron Letters
Volume	31
Issue number	15
DOIs	https://doi.org/10.1016/0040-4039(90)80103-s
State	Published - 1990

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10.1016/0040-4039(90)80103-s

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title = "Cine substitution in fused chlorocyclobutanones by N, S and C nucleophiles. Oxyallyl cations and an unusual diner formation.",

abstract = "Chlorocyclobutanone 1 was shown for the first time to react with S-, N-, and C-nucleophiles to produce cine substitution products, which apparently arise via an oxyallyl cation species 2. With some nucleophiles, the cine product is accompanied by an unusual dimer involving bond formation between two tertiary carbons.",

author = "Alfred Hassner and Simha Naidorf-Neir and Gottlieb, \{Hugo E.\}",

year = "1990",

doi = "10.1016/0040-4039(90)80103-s",

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AU - Naidorf-Neir, Simha

AU - Gottlieb, Hugo E.

PY - 1990

Y1 - 1990

N2 - Chlorocyclobutanone 1 was shown for the first time to react with S-, N-, and C-nucleophiles to produce cine substitution products, which apparently arise via an oxyallyl cation species 2. With some nucleophiles, the cine product is accompanied by an unusual dimer involving bond formation between two tertiary carbons.

AB - Chlorocyclobutanone 1 was shown for the first time to react with S-, N-, and C-nucleophiles to produce cine substitution products, which apparently arise via an oxyallyl cation species 2. With some nucleophiles, the cine product is accompanied by an unusual dimer involving bond formation between two tertiary carbons.

UR - https://www.scopus.com/pages/publications/0025213438

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DO - 10.1016/0040-4039(90)80103-s

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AN - SCOPUS:0025213438

SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Cine substitution in fused chlorocyclobutanones by N, S and C nucleophiles. Oxyallyl cations and an unusual diner formation.

Abstract

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