15158-56-2

Upstream product

• 280-65-9 bicyclo[3.3.1]nonane 
• 17530-61-9 bicyclo[3.3.1]non-1-ene 
• 63050-85-1 (+)-3-(3-Brompropyl)-cyclohexanon 
• 157774-18-0 1-nitroxybicyclo<3.3.1>nonane 
• 770-15-0 bicyclo[3.3.1]nonane-3,7-dione 
• 26917-97-5 bicyclo<3.3.1>nonane-1,endo-2-diol 
• 121455-35-4 1-hydroxybicyclo<3.3.1>non-endo-2-yl benzoate 
• 121455-37-6 endo-2-hydroxybicyclo<3.3.1>non-1-yl benzoate 
• 121455-49-0 1-hydroxybicyclo<3.3.1.>nonan-2-one 
• 17530-65-3 Bicyclo<3.3.1>non-1-yl-trimethylammoniumjodid 
• 20498-05-9 3-allylcyclohexanone 
• 930-68-7 cyclohexenone 
• 344765-63-5 4-(3-phenylselanyl-propyl)-octa-1,7-dien-4-ol 
• 344765-58-8 1-phenylselanyl-oct-7-en-4-ol 

Downstream Products

• 39170-77-9 Thiocarbonic acid O-bicyclo[3.3.1]non-1-yl ester O-p-tolyl ester 
• 87174-34-3 2-Imino-3-phenyl-3,5-diaza-tricyclo[5.3.3.0^1,5]tridecan-4-one 

Relevant academic research and scientific papers

Solvolysis of 2-Methylene Bicyclic Bridgehead Derivatives: A Model for Gradual Variation of ?-Conjugation in Carbocations

The rates of solvolysis in ethanol or 80percent ethanol at 25 deg C have been determined on 2-methylenebicyclooct-1-yl triflate (4a), 2-methylenebicyclooct-1-yl triflate (5a), 2-methylenebicyclonon-1-yl mesylate (6a), 2-methylenebicyclonon-1-yl mesylate (7a-OMs) and heptafluorobutyrate (7a-OHFB), 1-chloro-2-methylenebicyclodecane (8a), 2-methylenebicyclodec-1-yl trifluoroacetate (9a), and 4-methylene-3-homoadamantyl heptafluorobutyrate (10a) and on their corresponding parent 1-bicycloalkyl and 3-homoadamantyl derivatives 4b-10b containing the respective leaving group.The rate ratios for 4a/4b, 5a/5b, 10a/10b, 6a/6b, 7a/7b, 8a/8b, and 9a/9b are 10-3.9, 10-1.9, 10-1.1, 10-0.8, 100.9 (for mesylate), 10-0.2, and 100.7, respectively.A plot of the logarithms of the rate ratios against olefinic strain energies of their corresponding unsubstituted bridgehead olefins shows that the smaller the olefinic strain energy, the greater the rate ratio, providing a methodology to gradually change the conjugative ability of bridgehead carbocations.The enhancement of allylic conjugation with increasing skeletal flexibility has been further verified by the enhanced solvolysis rate of (E)-2-ethylidenebicyclonon-1-yl mesylate ((E)-6e) relative to 6a by a factor of 259.A similar study on much more rigid (E)-2-ethylidenebicyclooct-1-yl triflate ((E)-4e) gave a (E)-4e/4a rate ratio of 6.3.AM1 semiempirical molecular orbital calculations on pertinent 2-methylene and (E)-2-ethylidene bridgehead carbocations and corresponding hydrocarbons (L = hydrogen) also supported the increase in the conjugation with increasing skeletal flexibility.The solvolysis products were solely bridgehead substitution products, no indication for the formation of bridgehead olefin via an SN1' mechanism having been obtained.

Chemoselectivity of Nitroxylation of Cage Hydrocarbons

Abstract: The composition of reaction mixtures obtained by nitroxylation of 13 cage hydrocarbons with 100% nitric acid and its mixtures with acetic acid, acetic anhydride, and methylene chloride has been studied. More reactive substrates react with lowest

Aromatic derivative containing polycyclic alkane and organic electroluminescent device containing the derivative (by machine translation)

The invention relates to an aromatic derivative containing polycyclic alkane and an organic electroluminescent device containing the same, and the structure is shown in the following chemical formula I: The compound disclosed by the invention is an aromatic derivative containing a polycyclic alkane as a skeleton, exhibits excellent stability and high heat resistance; can greatly reduce energy loss, and can form a stable fused ring. The aromatic derivatives containing polycyclic alkanes can improve the stability. (by machine translation)

One-pot synthesis of cage alcohols

An efficient one-pot procedure has been developed for the synthesis of cage alcohols with hydroxy groups in the bridgehead positions. The procedure includes initial nitroxylation with nitric acid or a mixture of nitric acid with acetic acid and subsequent hydrolysis in the presence of urea.

Tandem ring-closing metathesis-radical cyclization based on 4-(phenylseleno)butanal and methyl 3-(phenylseleno)propanoate - A route to bicyclic compounds

α,ω-(Phenylseleno) carbonyl compounds, such as 4-(phenylseleno)butanal (1) and methyl 3-(phenylseleno)propanoate (2), are easily converted by anionic reactions into substances that undergo sequential ring-closing metathesis and radical cyclization, affording bicyclic products.

SYNTHESIS AND HYDROLYTIC TRANSFORMATIONS OF NITROXY DERIVATIVES OF HOMOADAMANTANE PROTOADAMANTANE AND BICYCLONONANE

Mono- and dinitroxy derivatives of homoadamantane, protoadamantane, and bicyclononane were synthesized by nitroxylation.A study was carried out on the reactivity of these hydrocarbons relative to nitric acid and the hydrolytic transformations of the products obtained.The acid-catalyzed skeletal rearrangement of 3,6-dinitroxyhomoadamantane to 3-nitroxymethyl-1-adamantanol proceeds with retention of the substituent at the carbon atom, at which the carbenium ion is generated.

A Facile Synthesis of Bicycloalkan-1-ols. Evidence for Organosamarium Intermediates in the Samarium(II) Iodide Promoted Intramolecular Barbier-Type Reaction

Samarium(II) iodide (SmI2) has been successfully employed as a reductive coupling agent for the intramolecular Barbier-type synthesis of bicycloalkan-1-ols.Thus, a variety of 3-(ω-iodoalkyl)cycloalkanones, upon treatment with SmI2 and a catalytic q

SYNTHESES OF BICYCLIC 1,2-DIOLS VIA THE RING-EXPANSION OF BRIDGEHEAD ALDEHYDES OF BICYCLOOCTANE AND BICYCLONONANES WITH BENZOYL TRIFLATE

Bridgehead aldehydes of bicyclooctane (11a), bicyclononane (12a), and bicyclononane (13a) have been subjected to acylative ring-expansion by using benzoyl trifluoromethanesulfonate (triflate) to give mixtures of two or three bicyclic