Reactions of 1,3‐dihaloadamantanes with diphenylphosphide ions by the S RN 1 mechanism. Competition between intermolecular and intramolecular electron transfer reactions
The reactivity of 1,3‐dihaloadamantanes with diphenylphosphide ions (Ph 2 P − ) in liquid ammonia was studied. 1,3‐Dichloroadamantane (1a), 1‐bromo‐3‐chloroadamantane (1b) and 1,3‐dibromoadamantane (1c) reacted with Ph 2 P − ions under photostimulation by the S RN 1 mechanism. Irradiation of 1c with...
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| Veröffentlicht in: | Journal of physical organic chemistry 1994-11, Vol.7 (11), p.610-614 |
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| container_title | Journal of physical organic chemistry |
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| creator | Lukach, Andres E. Santiago, Ana. N. Rossi, Roberto A. |
| description | The reactivity of 1,3‐dihaloadamantanes with diphenylphosphide ions (Ph
2
P
−
) in liquid ammonia was studied. 1,3‐Dichloroadamantane (1a), 1‐bromo‐3‐chloroadamantane (1b) and 1,3‐dibromoadamantane (1c) reacted with Ph
2
P
−
ions under photostimulation by the S
RN
1 mechanism. Irradiation of 1c without Ph
2
P
−
ions gave no reaction ( |
| doi_str_mv | 10.1002/poc.610071104 |
| format | Article |
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2
P
−
) in liquid ammonia was studied. 1,3‐Dichloroadamantane (1a), 1‐bromo‐3‐chloroadamantane (1b) and 1,3‐dibromoadamantane (1c) reacted with Ph
2
P
−
ions under photostimulation by the S
RN
1 mechanism. Irradiation of 1c without Ph
2
P
−
ions gave no reaction (<5%). Three products were found: 1,3‐bis(diphenyphosphinyl)adamantane (2), (3‐X‐1‐adamantyl)diphenylphosphine (X = Cl, 3a; X = Br, 3b) and 1‐adamantyldiphenylphosphine (4). Compounds 2 and 4 were formed by intramolecular electron transfer (ET) of the radical anion 3a
−·
(3b
−·
); whereas 3a (3b) were formed by intermolecular ET of this radical anion to the substrates. It was observed that the product distribution depends on the substrate and reaction conditions.</description><identifier>ISSN: 0894-3230</identifier><identifier>EISSN: 1099-1395</identifier><identifier>DOI: 10.1002/poc.610071104</identifier><language>eng</language><ispartof>Journal of physical organic chemistry, 1994-11, Vol.7 (11), p.610-614</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c824-28e67285bf93aafac2f0b922d16b9292064c07cd3afd6ab3340b376f9304e7453</citedby><cites>FETCH-LOGICAL-c824-28e67285bf93aafac2f0b922d16b9292064c07cd3afd6ab3340b376f9304e7453</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Lukach, Andres E.</creatorcontrib><creatorcontrib>Santiago, Ana. N.</creatorcontrib><creatorcontrib>Rossi, Roberto A.</creatorcontrib><title>Reactions of 1,3‐dihaloadamantanes with diphenylphosphide ions by the S RN 1 mechanism. Competition between intermolecular and intramolecular electron transfer reactions</title><title>Journal of physical organic chemistry</title><description>The reactivity of 1,3‐dihaloadamantanes with diphenylphosphide ions (Ph
2
P
−
) in liquid ammonia was studied. 1,3‐Dichloroadamantane (1a), 1‐bromo‐3‐chloroadamantane (1b) and 1,3‐dibromoadamantane (1c) reacted with Ph
2
P
−
ions under photostimulation by the S
RN
1 mechanism. Irradiation of 1c without Ph
2
P
−
ions gave no reaction (<5%). Three products were found: 1,3‐bis(diphenyphosphinyl)adamantane (2), (3‐X‐1‐adamantyl)diphenylphosphine (X = Cl, 3a; X = Br, 3b) and 1‐adamantyldiphenylphosphine (4). Compounds 2 and 4 were formed by intramolecular electron transfer (ET) of the radical anion 3a
−·
(3b
−·
); whereas 3a (3b) were formed by intermolecular ET of this radical anion to the substrates. It was observed that the product distribution depends on the substrate and reaction conditions.</description><issn>0894-3230</issn><issn>1099-1395</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1994</creationdate><recordtype>article</recordtype><recordid>eNpFUEtOwzAUtBBIlMKSvQ9Aij_5LlHFT6pAKt1HL86zYpTYkW1UdccRuAe34iSkfFczmvdmNBpCzjlbcMbE5ejUIp9YwTlLD8iMs6pKuKyyQzJjZZUmUkh2TE5CeGZsumXFjLyvEVQ0zgbqNOUX8uP1rTUd9A5aGMBGsBjo1sSOtmbs0O76sXNh7EyL9MvW7GjskD7R9QPldEDVgTVhWNClG0aMZh9OG4xbREuNjegH16N66cFTsO1e8vAv4USinyyTaoNGT_1vw1NypKEPePaDc7K5ud4s75LV4-398mqVqFKkiSgxL0SZNbqSABqU0KyphGh5PkElWJ4qVqhWgm5zaKRMWSOLfPpmKRZpJuck-Y5V3oXgUdejNwP4Xc1ZvR-6noau_4aWn41zdno</recordid><startdate>199411</startdate><enddate>199411</enddate><creator>Lukach, Andres E.</creator><creator>Santiago, Ana. N.</creator><creator>Rossi, Roberto A.</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>199411</creationdate><title>Reactions of 1,3‐dihaloadamantanes with diphenylphosphide ions by the S RN 1 mechanism. Competition between intermolecular and intramolecular electron transfer reactions</title><author>Lukach, Andres E. ; Santiago, Ana. N. ; Rossi, Roberto A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c824-28e67285bf93aafac2f0b922d16b9292064c07cd3afd6ab3340b376f9304e7453</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1994</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lukach, Andres E.</creatorcontrib><creatorcontrib>Santiago, Ana. N.</creatorcontrib><creatorcontrib>Rossi, Roberto A.</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of physical organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lukach, Andres E.</au><au>Santiago, Ana. N.</au><au>Rossi, Roberto A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reactions of 1,3‐dihaloadamantanes with diphenylphosphide ions by the S RN 1 mechanism. Competition between intermolecular and intramolecular electron transfer reactions</atitle><jtitle>Journal of physical organic chemistry</jtitle><date>1994-11</date><risdate>1994</risdate><volume>7</volume><issue>11</issue><spage>610</spage><epage>614</epage><pages>610-614</pages><issn>0894-3230</issn><eissn>1099-1395</eissn><abstract>The reactivity of 1,3‐dihaloadamantanes with diphenylphosphide ions (Ph
2
P
−
) in liquid ammonia was studied. 1,3‐Dichloroadamantane (1a), 1‐bromo‐3‐chloroadamantane (1b) and 1,3‐dibromoadamantane (1c) reacted with Ph
2
P
−
ions under photostimulation by the S
RN
1 mechanism. Irradiation of 1c without Ph
2
P
−
ions gave no reaction (<5%). Three products were found: 1,3‐bis(diphenyphosphinyl)adamantane (2), (3‐X‐1‐adamantyl)diphenylphosphine (X = Cl, 3a; X = Br, 3b) and 1‐adamantyldiphenylphosphine (4). Compounds 2 and 4 were formed by intramolecular electron transfer (ET) of the radical anion 3a
−·
(3b
−·
); whereas 3a (3b) were formed by intermolecular ET of this radical anion to the substrates. It was observed that the product distribution depends on the substrate and reaction conditions.</abstract><doi>10.1002/poc.610071104</doi><tpages>5</tpages></addata></record> |
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| ispartof | Journal of physical organic chemistry, 1994-11, Vol.7 (11), p.610-614 |
| issn | 0894-3230 1099-1395 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_poc_610071104 |
| source | Access via Wiley Online Library |
| title | Reactions of 1,3‐dihaloadamantanes with diphenylphosphide ions by the S RN 1 mechanism. Competition between intermolecular and intramolecular electron transfer reactions |
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