1979
DOI: 10.1139/v79-477
|View full text |Cite
|
Sign up to set email alerts
|

The transannular electrophilic reaction of alkenyl nitroso compounds and the stereochemistry of nitrosyl chloride addition

Abstract: Y C .~ L. CHOW, K , SO\I-\SEKHARA?< PILLAY, and H~R V E RTCITARL). Ca1-l. J. Chem. 57.2913Chem. 57. (1979.Nitrosql chloride reacted with :,5-c:.clooctadiene and trcir!. ~,tr.nrir,trr~i~.~-1,5,9-cyc1od~deca-triene i11 methglene chloride by the c,D-addition to g i~e chioronitroso al!tenes u.iik cis a n 2 thi-eo (tintis) configuraiion, respcctikely. These enantionioiphic C-nitrcso colnpounds were isolated as a single compor~iid for the fornier; and a n i i~t u r e io: the latter, of dl arid (or) inero din?ers, … Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1
1
1

Citation Types

0
5
0

Year Published

1980
1980
2011
2011

Publication Types

Select...
4
3

Relationship

1
6

Authors

Journals

citations
Cited by 8 publications
(5 citation statements)
references
References 0 publications
0
5
0
Order By: Relevance
“…Similar considerations have been applied to the reaction products of nitrosyl chloride and 1,5-cyclooctadiene and trans,trans,trans- cyclododecatriene . Ponder and Wheat studied the dimeric nitrosochloride products of the addition to the strained bicyclic olefins norbornene, norbornadiene, 5-methylene-2-norbornene, 5-ethylidene-2-norbornene, and bicyclo[2,2,2]octene-2.…”
Section: 3 Addition Reactions To Cc Double Bonds231 Addition Of Nitr...mentioning
confidence: 99%
See 1 more Smart Citation
“…Similar considerations have been applied to the reaction products of nitrosyl chloride and 1,5-cyclooctadiene and trans,trans,trans- cyclododecatriene . Ponder and Wheat studied the dimeric nitrosochloride products of the addition to the strained bicyclic olefins norbornene, norbornadiene, 5-methylene-2-norbornene, 5-ethylidene-2-norbornene, and bicyclo[2,2,2]octene-2.…”
Section: 3 Addition Reactions To Cc Double Bonds231 Addition Of Nitr...mentioning
confidence: 99%
“…Similar considerations have been applied to the reaction products of nitrosyl chloride and 1,5-cyclooctadiene and trans,trans,trans-cyclododecatriene. 97 Ponder and Wheat 98 studied the dimeric nitrosochloride products of the addition to the strained bicyclic olefins norbornene, norbornadiene, 5-methylene-2-norbornene, 5-ethylidene-2-norbornene, and bicyclo[2,2,2]octene-2. Other authors have given careful consideration to the stereochemistry of nitrosyl chloride addition products to various terpenes, e.g., γ-terpinene, 99 sylvestrene, 100 p-menth-1-ene, limonene and R-pinene, 101 (()-R-terpinyl acetate, 102 (+)-car-3-ene, 103 and transβ-terpineol.…”
Section: Addition Of Nitrosyl Halidesmentioning
confidence: 99%
“…The α-chlorooxime can eventually be hydrolyzed to α-chloroketone 4 or used in other ways. 3 The NOCl addition to alkene is shown to be trans 1-3 as well as cis, 5,6 and usually follows…”
Section: Methodsmentioning
confidence: 99%
“…(96) 216 Yuan L. Chow product, bianthrone. However, the observation that phenols are formed only in 'undried' benzene, and not in anhydrous benzene (equation 97)50, suggests that the thermally o r photolytically initiated hydrolysis of the corresponding nitrite may be the more probable pathway under the conditions.…”
Section: Nitro-nitrite Rearrangementmentioning
confidence: 99%
“…A poor yield of 218 is also obtained in the photolysis of 215 in ether. It appears that the pathways to 216 the nitro group is transmitted to the epoxide ring, causing ionization of a C-0 bond followed by a nitro group shift or HNO2 elimination. The competing pathway is hydrogen abstraction by the excited nitro group leading to a variety of reduction stages; at a certain stage the epoxide ring may be opened with the aid of electronic interactions or by another photoexcitation.…”
Section: Geminally Substituted Nitroalkanesmentioning
confidence: 99%