Term: bowsprit (flagpole) https://doi.org/10.1351/goldbook.B00719 Definition: In the boat form of cyclohexane and related structures there are two ring atoms lying out of the plane of the other four; exocyclic bonds to these two atoms pointing in a direction roughly parallel to that plane are called bowsprit, the other two are called flagpole. B00719.png Related Terms: 1) boat (http://doi.org/10.1351/goldbook.B00689). Image: Not defined (https://goldbook.iupac.org/img/inline/B00719.png) Source: PAC, 1996, 68, 2193. 'Basic terminology of stereochemistry (IUPAC Recommendations 1996)' on page 2201 (https://doi.org/10.1351/pac199668122193) Citation: 'bowsprit (flagpole)' in IUPAC Compendium of Chemical Terminology, 5th ed. International Union of Pure and Applied Chemistry; 2025. Online version 5.0.0, 2025. https://doi.org/10.1351/goldbook.B00719 License: The IUPAC Gold Book is licensed under Creative Commons Attribution-ShareAlike CC BY-SA 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) for individual terms. Disclaimer: The International Union of Pure and Applied Chemistry (IUPAC) is continuously reviewing and, where needed, updating terms in the Compendium of Chemical Terminology (the IUPAC Gold Book). Users of these terms are encouraged to include the version of a term with its use and to check regularly for updates to term definitions that you are using.