The Preparation and Properties of 1,2-Bis (triphenylphosphoranyl) benzocyclobutene

Alfred T. Blomquist; Victor J. Hruby

doi:10.1021/ja00995a030

The Preparation and Properties of 1,2-Bis (triphenylphosphoranyl) benzocyclobutene

Alfred T. Blomquist, Victor J. Hruby

Chemistry and Biochemistry

Research output: Contribution to journal › Article

20 Scopus citations

Abstract

The preparation of trans-1,2-bis(triphenylphosphonio)benzocyclobutene dibromide and its conversion to 1,2-bis(triphenylphosphoranyl)benzocyclobutene are described. Treatment of the dibromide salt with base followed by reaction with a benzaldehyde affords different results that depend upon the nature of the solvent. In ethanol as the major solvent, the principal products are the cis- and trans-1-benzylidenebenzocyclobutenes corresponding to the particular benzaldehyde used, together with triphenylphosphine oxide; in DMF or DMSO, the major products are the cis,cis- and/or cis,trans- and/or trans,trans-1,2-bisbenzylidenebenzocyclobutenes corresponding to the benzaldehydes used, as well as triphenylphosphine oxide. In both instances a number of minor products are obtained. The structure and stereochemistry of the major products are in accord with the chemical and physical data reported herein.

Original language	English (US)
Pages (from-to)	4996-5007
Number of pages	12
Journal	Journal of the American Chemical Society
Volume	89
Issue number	19
DOIs	https://doi.org/10.1021/ja00995a030
State	Published - Sep 1 1967

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja00995a030

Fingerprint Dive into the research topics of 'The Preparation and Properties of 1,2-Bis (triphenylphosphoranyl) benzocyclobutene'. Together they form a unique fingerprint.

Cite this

Blomquist, A. T., & Hruby, V. J. (1967). The Preparation and Properties of 1,2-Bis (triphenylphosphoranyl) benzocyclobutene. Journal of the American Chemical Society, 89(19), 4996-5007. https://doi.org/10.1021/ja00995a030

@article{e2e78ecf04b84b1baee4b657f77aedf9,

title = "The Preparation and Properties of 1,2-Bis (triphenylphosphoranyl) benzocyclobutene",

abstract = "The preparation of trans-1,2-bis(triphenylphosphonio)benzocyclobutene dibromide and its conversion to 1,2-bis(triphenylphosphoranyl)benzocyclobutene are described. Treatment of the dibromide salt with base followed by reaction with a benzaldehyde affords different results that depend upon the nature of the solvent. In ethanol as the major solvent, the principal products are the cis- and trans-1-benzylidenebenzocyclobutenes corresponding to the particular benzaldehyde used, together with triphenylphosphine oxide; in DMF or DMSO, the major products are the cis,cis- and/or cis,trans- and/or trans,trans-1,2-bisbenzylidenebenzocyclobutenes corresponding to the benzaldehydes used, as well as triphenylphosphine oxide. In both instances a number of minor products are obtained. The structure and stereochemistry of the major products are in accord with the chemical and physical data reported herein.",

author = "Blomquist, {Alfred T.} and Hruby, {Victor J.}",

year = "1967",

month = sep,

day = "1",

doi = "10.1021/ja00995a030",

language = "English (US)",

volume = "89",

pages = "4996--5007",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - The Preparation and Properties of 1,2-Bis (triphenylphosphoranyl) benzocyclobutene

AU - Blomquist, Alfred T.

AU - Hruby, Victor J.

PY - 1967/9/1

Y1 - 1967/9/1

N2 - The preparation of trans-1,2-bis(triphenylphosphonio)benzocyclobutene dibromide and its conversion to 1,2-bis(triphenylphosphoranyl)benzocyclobutene are described. Treatment of the dibromide salt with base followed by reaction with a benzaldehyde affords different results that depend upon the nature of the solvent. In ethanol as the major solvent, the principal products are the cis- and trans-1-benzylidenebenzocyclobutenes corresponding to the particular benzaldehyde used, together with triphenylphosphine oxide; in DMF or DMSO, the major products are the cis,cis- and/or cis,trans- and/or trans,trans-1,2-bisbenzylidenebenzocyclobutenes corresponding to the benzaldehydes used, as well as triphenylphosphine oxide. In both instances a number of minor products are obtained. The structure and stereochemistry of the major products are in accord with the chemical and physical data reported herein.

AB - The preparation of trans-1,2-bis(triphenylphosphonio)benzocyclobutene dibromide and its conversion to 1,2-bis(triphenylphosphoranyl)benzocyclobutene are described. Treatment of the dibromide salt with base followed by reaction with a benzaldehyde affords different results that depend upon the nature of the solvent. In ethanol as the major solvent, the principal products are the cis- and trans-1-benzylidenebenzocyclobutenes corresponding to the particular benzaldehyde used, together with triphenylphosphine oxide; in DMF or DMSO, the major products are the cis,cis- and/or cis,trans- and/or trans,trans-1,2-bisbenzylidenebenzocyclobutenes corresponding to the benzaldehydes used, as well as triphenylphosphine oxide. In both instances a number of minor products are obtained. The structure and stereochemistry of the major products are in accord with the chemical and physical data reported herein.

UR - http://www.scopus.com/inward/record.url?scp=0141670473&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0141670473&partnerID=8YFLogxK

U2 - 10.1021/ja00995a030

DO - 10.1021/ja00995a030

M3 - Article

AN - SCOPUS:0141670473

VL - 89

SP - 4996

EP - 5007

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 19

ER -