o-Carboranylcarbene and m-Carboranylcarbene

Sarangan L. Chari; Sheau Hwa Chiang; Maitland Jones

doi:10.1021/ja00375a033

o-Carboranylcarbene and m-Carboranylcarbene

Sarangan L. Chari, Sheau Hwa Chiang, Maitland Jones

Chemistry

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

29 Scopus citations

Abstract

Addition of o- and m-carboranylcarbene to olefins takes place in a largely stereospecific fashion. In the addition to cis olefins, it is the anti isomer that predominates. Insertion into carbon-hydrogen bonds occurs with a secondary/primary selectivity ratio of 3.0. (Methyl-o-carboranyl)carbene behaves like tolylcarbene in intramolecular reactions. It yields vinyl-o-carborane and the carborane analogue of benzocyclobutene. (Methyl-m-carboranyl)carbene does not give vinyl-m-carborane.

Original language	English (US)
Pages (from-to)	3138-3145
Number of pages	8
Journal	Journal of the American Chemical Society
Volume	104
Issue number	11
DOIs	https://doi.org/10.1021/ja00375a033
State	Published - 1982

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00375a033

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title = "o-Carboranylcarbene and m-Carboranylcarbene",

abstract = "Addition of o- and m-carboranylcarbene to olefins takes place in a largely stereospecific fashion. In the addition to cis olefins, it is the anti isomer that predominates. Insertion into carbon-hydrogen bonds occurs with a secondary/primary selectivity ratio of 3.0. (Methyl-o-carboranyl)carbene behaves like tolylcarbene in intramolecular reactions. It yields vinyl-o-carborane and the carborane analogue of benzocyclobutene. (Methyl-m-carboranyl)carbene does not give vinyl-m-carborane.",

author = "Chari, {Sarangan L.} and Chiang, {Sheau Hwa} and Maitland Jones",

year = "1982",

doi = "10.1021/ja00375a033",

language = "English (US)",

volume = "104",

pages = "3138--3145",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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TY - JOUR

T1 - o-Carboranylcarbene and m-Carboranylcarbene

AU - Chari, Sarangan L.

AU - Chiang, Sheau Hwa

AU - Jones, Maitland

PY - 1982

Y1 - 1982

N2 - Addition of o- and m-carboranylcarbene to olefins takes place in a largely stereospecific fashion. In the addition to cis olefins, it is the anti isomer that predominates. Insertion into carbon-hydrogen bonds occurs with a secondary/primary selectivity ratio of 3.0. (Methyl-o-carboranyl)carbene behaves like tolylcarbene in intramolecular reactions. It yields vinyl-o-carborane and the carborane analogue of benzocyclobutene. (Methyl-m-carboranyl)carbene does not give vinyl-m-carborane.

AB - Addition of o- and m-carboranylcarbene to olefins takes place in a largely stereospecific fashion. In the addition to cis olefins, it is the anti isomer that predominates. Insertion into carbon-hydrogen bonds occurs with a secondary/primary selectivity ratio of 3.0. (Methyl-o-carboranyl)carbene behaves like tolylcarbene in intramolecular reactions. It yields vinyl-o-carborane and the carborane analogue of benzocyclobutene. (Methyl-m-carboranyl)carbene does not give vinyl-m-carborane.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 11

ER -

o-Carboranylcarbene and m-Carboranylcarbene

Abstract

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