2,4-Dimethylmethano-2,4-didehydroadamantane (1) has been prepared and the gem-dimethyl substituent effects of propellane 1 in relation to its unsubstituted analogue 2 were studied. The reactivity of 1 is considerably greater than that of 2 due to the higher nucleophilicity of its central bond. However, 1 is thermally more stable than 2.

2,3-Methano-2,4-didehydro-11-homoadamantanone has been prepared quantitatively by an intramolecular cycloaddition of 2-methylene-5-oxo-4-homoadamantylidene.

AbstractThe hydroxydidehydrobrendane (I) is rearranged and then oxidized to form 4‐brenden‐2‐one (III).

A new [4.1.1]propellanone, 2,3-methano-2,4-didehydro-11-homoadamantanone (1), has been prepared quantitatively by an intramolecular cycloaddition of 2-methylene-5-oxo-4-homoadamantylidene, and its reactivity toward electrophiles and free radicals has been investigated. This is the smallest carbocyclic propellanone that has been prepared2.

Hitherto unknown 2,8-didehydro-9-noradamantanone (4) has been synthesized invilving oxa-di-π-methane photorearrangement of 4-brenden-2-one (3) as a key step.

Photooxygenation of α-diazocycloalkanones leads to ring contraction via Wolff rearrangement to give cycloakanones in moderate to good yields

AbstractThe hydroxynoradamantanone (I) is converted into the tosylhydrazone salt (VII) and the spirodiazirine (XIII) via the methylene ketone (V).

ChemInformVolume 20, Issue 51 Isocyclic Compounds ChemInform Abstract: A New, One-Pot Preparation of Alicyclic Ketones via Wolff Rearrangement. Z. MAJERSKI, Z. MAJERSKI Ruder Boskovic Inst., 41001 Zagreb, Croatia, YugoslaviaSearch for more papers by this authorV. VINKOVIC, V. VINKOVIC Ruder Boskovic Inst., 41001 Zagreb, Croatia, YugoslaviaSearch for more papers by this author Z. MAJERSKI, Z. MAJERSKI Ruder Boskovic Inst., 41001 Zagreb, Croatia, YugoslaviaSearch for more papers by this authorV. VINKOVIC, V. VINKOVIC Ruder Boskovic Inst., 41001 Zagreb, Croatia, YugoslaviaSearch for more papers by this author First published: December 19, 1989 https://doi.org/10.1002/chin.198951120Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume20, Issue51December 19, 1989 RelatedInformation

Photooxygenation of α-diazocycloalkanones leads to ring contraction via Wolff rearrangement to give cycloalkanones in moderate to good yields.

AbstractReaction of the title compound (I) with the symmetrical disulfides (II) yields the corresponding 2,4‐disulfenylated 2,4‐methanoadamantanes (III).

Gasphase thermolysis of the diazirine (I) yields the two isolable products (V) and (VI).

ADVERTISEMENT RETURN TO ISSUEPREVArticle1,7-Methanohomopentaprismane. A [2.2.1] propellaneZdenko Majerski, Jelena Veljkovic, and Mira KaseljCite this: J. Org. Chem. 1988, 53, 11, 2662–2664Publication Date (Print):May 1, 1988Publication History Published online1 May 2002Published inissue 1 May 1988https://pubs.acs.org/doi/10.1021/jo00246a061https://doi.org/10.1021/jo00246a061research-articleACS PublicationsRequest reuse permissionsArticle Views105Altmetric-Citations11LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTIntramolecular carbene chemistry. Evidence for exclusive C-H insertion in 8-methylene-2-noradamantylideneZdenko Majerski, Zdenko Hamersak, and Ruza Sarac-ArneriCite this: J. Org. Chem. 1988, 53, 21, 5053–5058Publication Date (Print):October 1, 1988Publication History Published online1 May 2002Published inissue 1 October 1988https://pubs.acs.org/doi/10.1021/jo00256a028https://doi.org/10.1021/jo00256a028research-articleACS PublicationsRequest reuse permissionsArticle Views370Altmetric-Citations7LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

ChemInformVolume 18, Issue 43 Physical Organic Chemistry ChemInform Abstract: Electronic Structure of 2,4-Methano-2,4-didehydroadamantane: A (3.1.1)-Propellane. Photoelectron and Semiempirical Studies. M. ECKERT-MAKSIC, M. ECKERT-MAKSIC Dep. Inorg. Chem., Univ. Melbourne, Victoria 3052, Aust.Search for more papers by this authorK. MLINARIC-MAJERSKI, K. MLINARIC-MAJERSKI Dep. Inorg. Chem., Univ. Melbourne, Victoria 3052, Aust.Search for more papers by this authorZ. MAJERSKI, Z. MAJERSKI Dep. Inorg. Chem., Univ. Melbourne, Victoria 3052, Aust.Search for more papers by this author M. ECKERT-MAKSIC, M. ECKERT-MAKSIC Dep. Inorg. Chem., Univ. Melbourne, Victoria 3052, Aust.Search for more papers by this authorK. MLINARIC-MAJERSKI, K. MLINARIC-MAJERSKI Dep. Inorg. Chem., Univ. Melbourne, Victoria 3052, Aust.Search for more papers by this authorZ. MAJERSKI, Z. MAJERSKI Dep. Inorg. Chem., Univ. Melbourne, Victoria 3052, Aust.Search for more papers by this author First published: October 27, 1987 https://doi.org/10.1002/chin.198743039AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume18, Issue43October 27, 1987 RelatedInformation

AbstractPyrolysis of the tosylhydrazone Na salt (I) yields via the intermediate carbene the title compound (II) (MS, IR, 1H, and 13C NMR).

The propellane (I) undergoes Ag(I)‐induced rearrangement to give the isomeric dimers (II) and (III).